首页 > 最新文献

Advanced Synthesis & Catalysis最新文献

英文 中文
Front Cover Picture: Merging Organolithium Chemistry and Stereoselective Biocatalysis: Transformation of Aromatic Nitriles into Chiral Alcohols (Adv. Synth. Catal. 14/2024) 有机锂化学与立体选择性生物催化的结合:将芳香族腈转化为手性醇。
IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-22 DOI: 10.1002/adsc.202400776
Nicolás Ríos-Lombardía, Gloria Morís-Menéndez, Iván Lavandera, Vicente Gotor-Fernández, Joaquín García-Álvarez

The front cover illustrates the cooperative action between organolithium reagents (RLi) and alcohol dehydrogenases (ADHs). This chemoenzymatic strategy facilitates the conversion of a range of aromatic nitriles into chiral alcohols. The critical aspect of this research was identifying optimal conditions that allow both RLi and ADHs to function effectively in the same reaction vessel. Details of the studies can be found in the research article by Joaquín García-Álvarez and co-workers (N. Ríos-Lombardía, G. Morís-Menéndez, I. Lavandera, V. Gotor-Fernández, J. García-Álvarez, Adv. Synth. Catal. 2024, 366, 3144–3152; DOI: 10.1002/adsc.202400460)

封面展示了有机锂试剂(RLi)与醇脱氢酶(ADHs)之间的合作作用。这种化学酶促策略有助于将一系列芳香族腈转化为手性醇。这项研究的关键是确定最佳条件,使 RLi 和 ADH 在同一反应容器中有效发挥作用。研究详情可参见 Joaquín García-Álvarez 及其合作者的研究文章(N. Ríos-Lombardía、G. Morís-Menéndez、I. Lavandera、V. Gotor-Fernández、J. García-Álvarez, Adv. Synth.Catal.2024, 366, XXXX-XXXX; DOI: 10.1002/adsc.202400460)
{"title":"Front Cover Picture: Merging Organolithium Chemistry and Stereoselective Biocatalysis: Transformation of Aromatic Nitriles into Chiral Alcohols (Adv. Synth. Catal. 14/2024)","authors":"Nicolás Ríos-Lombardía,&nbsp;Gloria Morís-Menéndez,&nbsp;Iván Lavandera,&nbsp;Vicente Gotor-Fernández,&nbsp;Joaquín García-Álvarez","doi":"10.1002/adsc.202400776","DOIUrl":"10.1002/adsc.202400776","url":null,"abstract":"<p>The front cover illustrates the cooperative action between organolithium reagents (RLi) and alcohol dehydrogenases (ADHs). This chemoenzymatic strategy facilitates the conversion of a range of aromatic nitriles into chiral alcohols. The critical aspect of this research was identifying optimal conditions that allow both RLi and ADHs to function effectively in the same reaction vessel. Details of the studies can be found in the research article by Joaquín García-Álvarez and co-workers (N. Ríos-Lombardía, G. Morís-Menéndez, I. Lavandera, V. Gotor-Fernández, J. García-Álvarez, <i>Adv. Synth. Catal</i>. <b>2024</b>, <i>366</i>, 3144–3152; DOI: 10.1002/adsc.202400460)\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":4.4,"publicationDate":"2024-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400776","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141754292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cp*Rh(III)-Catalyzed Divergent Synthesis of N-heterocycles with N-methoxyindoleamides and Isoxazolones Cp*Rh(III)-Catalyzed Divergent Synthesis of N-heterocycles with N-methoxyindoleamides and Isoxazolones(Cp*Rh(III)催化的 N-甲氧基吲哚酰胺和异噁唑酮与 N-杂环的歧化合成
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-20 DOI: 10.1002/adsc.202400425
Shang-Shi Zhang, Dan-Ting Shen, Wen-Xuan Zou, Shao-Yong Chen, Lin Xiao, Qiong Hu, Jia-Lin Song, Xu-Ge Liu
A method for synthesizing pyrimido[1,2-a]indol-4-ol heteroarenes via a Cp*Rh(III)-catalyzed cascade C-H activation/annulation strategy employing N-methoxyindoleamides and isoxazolones is developed. Also, a framework of 3-methoxy-2,3-dihydro-[1,3,5]triazino[1,2-a]indole-4,10-dione was successfully synthesized via a Cp*Rh-catalyzed C-H activation/annulation/oxidation reaction between N-(methyloxy)-1H-indole-1-carboxamide and isoxazolones. These reactions demonstrated the suitability of several substrates, compatibility with numerous functional groups, and mild reaction conditions. Preliminary mechanistic investigations have been completed.
利用 N-甲氧基吲哚酰胺和异噁唑酮,通过 Cp*Rh(III)-catalyzed cascade C-H activation/annulation 策略,开发了一种合成嘧啶并[1,2-a]吲哚-4-醇杂环戊烯的方法。此外,通过 N-(甲氧基)-1H-吲哚-1-甲酰胺和异噁唑酮之间的 Cp*Rh 催化 C-H 活化/环化/氧化反应,成功合成了 3-甲氧基-2,3-二氢-[1,3,5]三嗪并[1,2-a]吲哚-4,10-二酮的框架。这些反应证明了多种底物的适用性、与多种官能团的兼容性以及温和的反应条件。初步的机理研究已经完成。
{"title":"Cp*Rh(III)-Catalyzed Divergent Synthesis of N-heterocycles with N-methoxyindoleamides and Isoxazolones","authors":"Shang-Shi Zhang, Dan-Ting Shen, Wen-Xuan Zou, Shao-Yong Chen, Lin Xiao, Qiong Hu, Jia-Lin Song, Xu-Ge Liu","doi":"10.1002/adsc.202400425","DOIUrl":"https://doi.org/10.1002/adsc.202400425","url":null,"abstract":"A method for synthesizing pyrimido[1,2-a]indol-4-ol heteroarenes via a Cp*Rh(III)-catalyzed cascade C-H activation/annulation strategy employing N-methoxyindoleamides and isoxazolones is developed. Also, a framework of 3-methoxy-2,3-dihydro-[1,3,5]triazino[1,2-a]indole-4,10-dione was successfully synthesized via a Cp*Rh-catalyzed C-H activation/annulation/oxidation reaction between N-(methyloxy)-1H-indole-1-carboxamide and isoxazolones. These reactions demonstrated the suitability of several substrates, compatibility with numerous functional groups, and mild reaction conditions. Preliminary mechanistic investigations have been completed.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141730706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis, Characterization and Biological Evaluation of 3‐Oxo‐pyrimido[1,2‐b]indazoles 3-Oxo-primido[1,2-b]indazoles 的合成、表征和生物学评价
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-20 DOI: 10.1002/adsc.202400739
Xinyu Zhang, Xuan Zhao, Die Wu, Jingsa Zhang, Yilu Shou, Xingya Wang, Yongmin Ma, Bihong Zhu
The synthesis of substituted 3‐oxo‐pyrimido[1,2‐b]indazoles from 3‐aminoindazoles and ketones has been established. It involves one molecule of 3‐aminoindazoles and two molecules of ketones via a [3+2+1] three‐component annulation process. 3‐Oxo‐pyrimido[1,2‐b]indazoles exhibit strong yellow fluorescence in various solvents. A wide range of products have anti‐oxidant activities. Cytotoxicity studies indicate that compounds 3a, 3aa and 3ab have obvious effects on both HCT116 and A549 cancer cell lines.
由 3-氨基吲唑和酮合成取代的 3-氧代嘧啶并[1,2-b]吲唑的方法已经建立。它涉及一个分子的 3-氨基吲唑和两个分子的酮,通过[3+2+1]三组份环化过程合成。3- 氧代嘧啶并[1,2-b]吲唑在各种溶剂中都能发出强烈的黄色荧光。多种产品具有抗氧化活性。细胞毒性研究表明,化合物 3a、3aa 和 3ab 对 HCT116 和 A549 癌细胞株都有明显的作用。
{"title":"Synthesis, Characterization and Biological Evaluation of 3‐Oxo‐pyrimido[1,2‐b]indazoles","authors":"Xinyu Zhang, Xuan Zhao, Die Wu, Jingsa Zhang, Yilu Shou, Xingya Wang, Yongmin Ma, Bihong Zhu","doi":"10.1002/adsc.202400739","DOIUrl":"https://doi.org/10.1002/adsc.202400739","url":null,"abstract":"The synthesis of substituted 3‐oxo‐pyrimido[1,2‐b]indazoles from 3‐aminoindazoles and ketones has been established. It involves one molecule of 3‐aminoindazoles and two molecules of ketones via a [3+2+1] three‐component annulation process. 3‐Oxo‐pyrimido[1,2‐b]indazoles exhibit strong yellow fluorescence in various solvents. A wide range of products have anti‐oxidant activities. Cytotoxicity studies indicate that compounds 3a, 3aa and 3ab have obvious effects on both HCT116 and A549 cancer cell lines.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141732617","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Dearomative 1,2-(Deutero)Hydrotrifluoromethylation of Chromium-Bound Arenes 铬结合烯类的 1,2-(脱氘代)氢三氟甲基化反应
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-19 DOI: 10.1002/adsc.202400718
Cheng-Jie Wu, Xu Jiang, Jia-Yi Qiu, Ming-Yang Wang, Wei Li
Dearomative trifluoromethylation of arenes provides an ideal method for constructing CF3-containing three-dimensional architectures which are of increasing interest in drug discovery. However, such transformation is rare and challenging because of the inherently low reactivity of arene π-systems and selectivity issues. Herein, we disclose a general dearomative 1,2-hydrotrifluoromethylation of (hetero)arenes utilizing activation by temporary π-complexation to chromium, thus affording convenient access to 1,3-cyclohexadienes bearing the privileged CF3 group. The versatility of this strategy further enables a dearomative 1,2-deuterotrifluoromethylation with high deuterated ratios. The related dearomative 1,2-(deutero)hydroperfluoroethylation reactions were conducted well for a range of chromium-bound (hetero)arenes. Finally, a reasonable mechanism was proposed based on the intermediate capture and control experiments.
炔烃的三氟甲基化反应(Dearomative trifluoromethylation of arenes)为构建含 CF3 的三维结构提供了一种理想的方法,这种结构在药物发现中的应用越来越受到关注。然而,由于炔烃 π 系统固有的低反应活性和选择性问题,这种转化非常罕见且具有挑战性。在此,我们揭示了一种利用与铬的临时π-络合活化对(杂)炔类化合物进行一般脱芳1,2-氢三氟甲基化的方法,从而方便地获得带有特选CF3基团的1,3-环己二烯。这种策略的多功能性进一步实现了高氚化比率的 1,2-氚三氟甲基化反应。对于一系列铬结合(杂)烷,相关的 1,2-(氘代)氢全氟乙基化反应进行得很好。最后,根据中间体捕获和控制实验提出了合理的机理。
{"title":"Dearomative 1,2-(Deutero)Hydrotrifluoromethylation of Chromium-Bound Arenes","authors":"Cheng-Jie Wu, Xu Jiang, Jia-Yi Qiu, Ming-Yang Wang, Wei Li","doi":"10.1002/adsc.202400718","DOIUrl":"https://doi.org/10.1002/adsc.202400718","url":null,"abstract":"Dearomative trifluoromethylation of arenes provides an ideal method for constructing CF3-containing three-dimensional architectures which are of increasing interest in drug discovery. However, such transformation is rare and challenging because of the inherently low reactivity of arene π-systems and selectivity issues. Herein, we disclose a general dearomative 1,2-hydrotrifluoromethylation of (hetero)arenes utilizing activation by temporary π-complexation to chromium, thus affording convenient access to 1,3-cyclohexadienes bearing the privileged CF3 group. The versatility of this strategy further enables a dearomative 1,2-deuterotrifluoromethylation with high deuterated ratios. The related dearomative 1,2-(deutero)hydroperfluoroethylation reactions were conducted well for a range of chromium-bound (hetero)arenes. Finally, a reasonable mechanism was proposed based on the intermediate capture and control experiments.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141726464","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Organophotocatalyzed C-Si Bond Fragmentation Using Silyl Ethers as Radical Precursors 使用硅基醚作为自由基前驱体的有机光催化 C-Si 键断裂法
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-19 DOI: 10.1002/adsc.202400584
Adrian Luguera Ruiz, Valentina Benazzi, Federico Tucci, Francesca Rizzo, Daniele Merli, Stefano Protti, Maurizio Fagnoni
In this work, silyl ethers of phenols and alcohols have been successfully prepared and tested as neutral carbon (silicon) centered radical precursors. The organocophotocatalyzed oxidation (by the Fukuzumi catalyst) of these ethers caused the cleavage of a C-Si (or a Si-Si) bond for the release of the desired radical to be used for the forging of C(sp3)-C(sp3) (or C(sp3)-Si) bonds via a Giese reaction.
在这项工作中,成功制备了苯酚和醇的硅基醚,并将其作为以碳(硅)为中心的中性自由基前体进行了测试。通过 Fukuzumi 催化剂对这些醚进行有机光催化氧化,导致 C-Si(或 Si-Si)键断裂,从而释放出所需自由基,并通过 Giese 反应锻造出 C(sp3)-C(sp3)(或 C(sp3)-Si)键。
{"title":"Organophotocatalyzed C-Si Bond Fragmentation Using Silyl Ethers as Radical Precursors","authors":"Adrian Luguera Ruiz, Valentina Benazzi, Federico Tucci, Francesca Rizzo, Daniele Merli, Stefano Protti, Maurizio Fagnoni","doi":"10.1002/adsc.202400584","DOIUrl":"https://doi.org/10.1002/adsc.202400584","url":null,"abstract":"In this work, silyl ethers of phenols and alcohols have been successfully prepared and tested as neutral carbon (silicon) centered radical precursors. The organocophotocatalyzed oxidation (by the Fukuzumi catalyst) of these ethers caused the cleavage of a C-Si (or a Si-Si) bond for the release of the desired radical to be used for the forging of C(sp3)-C(sp3) (or C(sp3)-Si) bonds via a Giese reaction.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141726463","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Metal-free photocyclization/oxidation cascade constructing quinoline-2-ones and tetrahydrocarbazolones 构建喹啉-2-酮和四氢咔唑酮的无金属光环化/氧化级联反应
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-19 DOI: 10.1002/adsc.202400525
Yanke Hao, He Huang
We reported a one-pot photocyclization/ oxidation cascade of N-aryl acrylamides to afford quinoline-2-ones. Thioxanthone was used as a bifunctional energy transfer agent to mediate both photocyclization and generation of singlet oxygen, the latter facilitates the dehydrogenation of dihydroquinoline-2-one intermediate. This cascade strategy also supports the 5-endo-trig cyclization to synthesize tetrahydrocarbazolones from phenylamino cyclohexenones.
我们报告了一种 N-芳基丙烯酰胺的一锅式光环化/氧化级联反应,从而得到喹啉-2-酮。硫杂蒽酮被用作一种双功能能量转移剂,既可介导光环化,又可生成单线态氧,后者可促进二氢喹啉-2-酮中间体的脱氢反应。这种级联策略还支持从苯基氨基环己烯酮合成四氢咔唑酮的 5-endo-trig 环化反应。
{"title":"Metal-free photocyclization/oxidation cascade constructing quinoline-2-ones and tetrahydrocarbazolones","authors":"Yanke Hao, He Huang","doi":"10.1002/adsc.202400525","DOIUrl":"https://doi.org/10.1002/adsc.202400525","url":null,"abstract":"We reported a one-pot photocyclization/ oxidation cascade of N-aryl acrylamides to afford quinoline-2-ones. Thioxanthone was used as a bifunctional energy transfer agent to mediate both photocyclization and generation of singlet oxygen, the latter facilitates the dehydrogenation of dihydroquinoline-2-one intermediate. This cascade strategy also supports the 5-endo-trig cyclization to synthesize tetrahydrocarbazolones from phenylamino cyclohexenones.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141726466","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Neighboring π-Coordination in Palladium Catalyzed [4+4] Cycloaddition of γ-Methylidene-δ-Valerolactones with Divinylketones 钯催化γ-亚甲基-δ-戊内酯与二乙烯酮的[4+4]环加成中的邻π配位
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-19 DOI: 10.1002/adsc.202400234
Xiaoying Wu, Wei Feng, Jiayi Zhao, Daoshan Yang, Ran Song, Wen Si, Jian Lv
A palladium-catalyzed [4+4] cycloaddition of aryl-substituted γ-methylidene-δ-valerolactones (GMDVs) with divinylke-tones (DVKs) was developed, providing an approach to access various mono-cyclic tetrahydro-2H-oxocines with diverse substituents in up to 95% yields and >20:1 dr. This reaction was facilitated by anchoring olefin (C=C) at the α-position of carbonyls.
研究人员开发了一种钯催化的芳基取代的γ-亚甲基-δ-戊内酯(GMDVs)与二乙烯基酮(DVKs)的[4+4]环加成反应,提供了一种以高达95%的收率和20:1的比值获得具有不同取代基的各种单环四氢-2H-氧杂环己烷的方法。
{"title":"Neighboring π-Coordination in Palladium Catalyzed [4+4] Cycloaddition of γ-Methylidene-δ-Valerolactones with Divinylketones","authors":"Xiaoying Wu, Wei Feng, Jiayi Zhao, Daoshan Yang, Ran Song, Wen Si, Jian Lv","doi":"10.1002/adsc.202400234","DOIUrl":"https://doi.org/10.1002/adsc.202400234","url":null,"abstract":"A palladium-catalyzed [4+4] cycloaddition of aryl-substituted γ-methylidene-δ-valerolactones (GMDVs) with divinylke-tones (DVKs) was developed, providing an approach to access various mono-cyclic tetrahydro-2H-oxocines with diverse substituents in up to 95% yields and &gt;20:1 dr. This reaction was facilitated by anchoring olefin (C=C) at the α-position of carbonyls.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141726462","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of Acyl Halides from Carboxylic Acid Thioesters for Synthesis of Ketones, Esters, Amides and Peptides 从羧酸硫酯合成酰卤,用于合成酮、酯、酰胺和肽
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-19 DOI: 10.1002/adsc.202400531
Shuji Nagano, Keiji Maruoka
A synthesis of acyl halides from the corresponding carboxylic acid thioesters was achieved using commercially available Selectfluor or NCS, and the acyl fluoride or chloride intermediates were transformed to the corresponding esters, amides, and several carbon-carbon bond formation products. This approach can be applied to the peptide synthesis from functionalized amino acid thioesters.
使用市售的 Selectfluor 或 NCS 实现了从相应的羧酸硫酯合成酰基卤化物,酰基氟化物或氯化物中间体转化为相应的酯、酰胺和多种碳-碳键形成产物。这种方法可用于从官能化氨基酸硫代酯合成肽。
{"title":"Synthesis of Acyl Halides from Carboxylic Acid Thioesters for Synthesis of Ketones, Esters, Amides and Peptides","authors":"Shuji Nagano, Keiji Maruoka","doi":"10.1002/adsc.202400531","DOIUrl":"https://doi.org/10.1002/adsc.202400531","url":null,"abstract":"A synthesis of acyl halides from the corresponding carboxylic acid thioesters was achieved using commercially available Selectfluor or NCS, and the acyl fluoride or chloride intermediates were transformed to the corresponding esters, amides, and several carbon-carbon bond formation products. This approach can be applied to the peptide synthesis from functionalized amino acid thioesters.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141726465","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cu‐catalyzed Formal Addition of Aliphatic C(sp3)–H Bonds to Alkenes via Phenyl Radical Involved Intermolecular HAT 铜催化脂肪族 C(sp3)-H键与烯烃通过苯基自由基参与分子间 HAT 的正规加成反应
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-19 DOI: 10.1002/adsc.202400377
Peizhi Bai, Xin Zhang, Qinshuang Su, Tiebo Xiao, Yubo Jiang, Guoying Zhang, Yinjun Xie, Guiping Qin
A copper catalyzed aerobic formal addition of aliphatic C(sp3)–H bonds to alkenes via a phenyl radical mediated intermolecular HAT process is reported herein, in which the phenylhydrazine not only acts as a good HAT reagent precursor but also as an excellent hydrogen atom donor. This reaction affords an alternative method for the direct formal addition of the aliphatic C(sp3)–H bonds to alkenes utilizing air as the radical initiator without additional reductants at the ambient temperature. A variety of alkanes and electron‐deficient alkenes are successfully incorporated, furnishing a series of aliphatic C(sp3)–H formal addition products in 20‐93% yields. The preliminary mechanistic studies uncover that the 2‐tetrahydrofuranyl and phenyl radical are formed in this reaction.
本文报告了一种铜催化的脂肪族 C(sp3)-H 键与烯烃通过苯基自由基介导的分子间 HAT 过程进行有氧形式加成的方法,其中苯肼不仅是一种良好的 HAT 试剂前体,还是一种极佳的氢原子供体。该反应提供了一种替代方法,利用空气作为自由基引发剂,在环境温度下无需额外的还原剂,即可直接将脂肪族 C(sp3)-H 键与烯烃进行形式加成。多种烷烃和缺电子烯烃被成功加入,生成了一系列脂肪族 C(sp3)-H 形式加成产物,产率为 20-93%。初步机理研究发现,在该反应中形成了 2-四氢呋喃基和苯基自由基。
{"title":"Cu‐catalyzed Formal Addition of Aliphatic C(sp3)–H Bonds to Alkenes via Phenyl Radical Involved Intermolecular HAT","authors":"Peizhi Bai, Xin Zhang, Qinshuang Su, Tiebo Xiao, Yubo Jiang, Guoying Zhang, Yinjun Xie, Guiping Qin","doi":"10.1002/adsc.202400377","DOIUrl":"https://doi.org/10.1002/adsc.202400377","url":null,"abstract":"A copper catalyzed aerobic formal addition of aliphatic C(sp3)–H bonds to alkenes via a phenyl radical mediated intermolecular HAT process is reported herein, in which the phenylhydrazine not only acts as a good HAT reagent precursor but also as an excellent hydrogen atom donor. This reaction affords an alternative method for the direct formal addition of the aliphatic C(sp3)–H bonds to alkenes utilizing air as the radical initiator without additional reductants at the ambient temperature. A variety of alkanes and electron‐deficient alkenes are successfully incorporated, furnishing a series of aliphatic C(sp3)–H formal addition products in 20‐93% yields. The preliminary mechanistic studies uncover that the 2‐tetrahydrofuranyl and phenyl radical are formed in this reaction.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141730607","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enzyme Cascade with Four Enzymes in One Pot for the Synthesis of L‐Phosphinothricin 一锅四酶合成 L-膦丝菌素的酶级联反应
IF 5.4 2区 化学 Q2 CHEMISTRY, APPLIED Pub Date : 2024-07-18 DOI: 10.1002/adsc.202400498
jianmiao xu, Zhijie Xi, Keji Keji Zhao, Chenxiang He, Feng Cheng, Ya-Ping Xue, Yu-Guo Zheng
The biocatalytic oxidative deamination‐ reductive amination process for the production of L‐phosphinothricin (L‐PPT) from D,L‐phosphinothricin (D,L‐PPT) is a green and environmentally friendly approach with significant development potential. In this study, the adopted technological route involves the oxidative deamination of the D‐PPT component in D,L‐PPT to 2‐oxo‐4‐(hydroxymethylphosphinyl)butanoic acid (PPO) by utilizing D‐amino acid oxidase (DAAO), fol‐lowed by the catalytic reductive amination of PPO to L‐PPT using phosphinothricin dehydrogenase (PpDH). In order to enhance the catalytic rate and reduce the inhibitory effect of the intermediate product PPO on the catalytic process, optimization of both oxidative deamination and reductive amination phases was conducted through separate strategies of constant‐pressure oxygen supply and substrate feeding, respectively. A "two‐step one‐pot" method was employed to link the optimized reactions, significantly shortening the production time. Furthermore, the "two‐step one‐pot" catalytic strategy was optimized, ultimately achieving a high 97.7% yield of L‐PPT with ee of L‐PPT >99.9% after 5.5 h of reaction under 800 mM D,L‐PPT catalytic conditions,further enchanced the catalytic efficiency and product yield.The aforementioned results demonstrate that this proposed approach has great potential for industrial‐scale production of L‐PPT as well as significant competitive advantages in terms of economic feasibility.
利用生物催化氧化脱氨-还原胺化工艺从 D,L-膦丝菌素(D,L-PPT)生产 L-膦丝菌素(L-PPT)是一种绿色环保的方法,具有巨大的发展潜力。本研究采用的技术路线是利用 D-氨基酸氧化酶(DAAO)将 D,L-PPT中的 D-PPT成分氧化脱氨成 2-氧代-4-(羟甲基膦酰基)丁酸(PPO),然后利用膦三嗪脱氢酶(PpDH)将 PPO催化还原胺化成 L-PPT。为了提高催化速率并减少中间产物 PPO 对催化过程的抑制作用,研究人员分别通过恒压供氧和底物喂入两种策略对氧化脱氨和还原胺化两个阶段进行了优化。采用 "两步一锅法 "将优化后的反应连接起来,大大缩短了生产时间。上述结果表明,该方法具有工业化生产 L-PPT 的巨大潜力,在经济可行性方面也具有显著的竞争优势。
{"title":"Enzyme Cascade with Four Enzymes in One Pot for the Synthesis of L‐Phosphinothricin","authors":"jianmiao xu, Zhijie Xi, Keji Keji Zhao, Chenxiang He, Feng Cheng, Ya-Ping Xue, Yu-Guo Zheng","doi":"10.1002/adsc.202400498","DOIUrl":"https://doi.org/10.1002/adsc.202400498","url":null,"abstract":"The biocatalytic oxidative deamination‐ reductive amination process for the production of L‐phosphinothricin (L‐PPT) from D,L‐phosphinothricin (D,L‐PPT) is a green and environmentally friendly approach with significant development potential. In this study, the adopted technological route involves the oxidative deamination of the D‐PPT component in D,L‐PPT to 2‐oxo‐4‐(hydroxymethylphosphinyl)butanoic acid (PPO) by utilizing D‐amino acid oxidase (DAAO), fol‐lowed by the catalytic reductive amination of PPO to L‐PPT using phosphinothricin dehydrogenase (PpDH). In order to enhance the catalytic rate and reduce the inhibitory effect of the intermediate product PPO on the catalytic process, optimization of both oxidative deamination and reductive amination phases was conducted through separate strategies of constant‐pressure oxygen supply and substrate feeding, respectively. A \"two‐step one‐pot\" method was employed to link the optimized reactions, significantly shortening the production time. Furthermore, the \"two‐step one‐pot\" catalytic strategy was optimized, ultimately achieving a high 97.7% yield of L‐PPT with ee of L‐PPT >99.9% after 5.5 h of reaction under 800 mM D,L‐PPT catalytic conditions,further enchanced the catalytic efficiency and product yield.The aforementioned results demonstrate that this proposed approach has great potential for industrial‐scale production of L‐PPT as well as significant competitive advantages in terms of economic feasibility.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141726144","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
期刊
Advanced Synthesis & Catalysis
全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1