Pub Date : 2025-05-01Epub Date: 2024-05-25DOI: 10.1016/j.gresc.2024.05.006
Dayuan Wang , Jiayi Zong , Bowen Wang , Longwu Sun , Xiao Xiao , Huri Piao , Miaolin Ke , Fener Chen
Axially chiral anilide compounds are an emerging but scarcely investigated class of stereogenic molecules with potential applications as chiral catalysts, biologically active scaffolds and functional materials. Compared to the C–C axially chiral molecules, the synthesis of axially chiral anilide compounds is a challenge owing to the lower rotation barriers. Herein, the construction of chiral allylic amine bearing axial chirality and central chirality via Pd-catalyzed atroposelective N-allylic alkylation reaction of cyclic vinyl carbonates and sulfonamides is reported. A diverse range of chiral sulfonamides bearing axial chirality and central chirality were synthesized in high yields and excellent enantioselectivities (up to 92 % yield and 99 % ee). In addition, the practical application of this protocol was also demonstrated by gram-scale synthesis and derivatives of the compound.
轴向手性苯胺类化合物是一类新兴的立体分子，在手性催化剂、生物活性支架和功能材料等方面具有潜在的应用前景。与C-C轴手性分子相比，由于轴手性苯胺化合物的旋转势垒较低，因此合成轴手性苯胺化合物是一个挑战。本文报道了通过pd催化环碳酸乙烯酯和磺胺类化合物的atroopselective n -烯丙基烷基化反应，构建具有轴向手性和中心手性的手性烯丙基胺。合成了一系列具有轴向手性和中心手性的手性磺胺类化合物，收率高，对映选择性好（产率高达92%，ee高达99%）。此外，该方案的实际应用也通过该化合物的克级合成和衍生物得到了验证。
{"title":"Asymmetric synthesis of allylic sulfonamides with axially and central chirality via palladium-catalyzed of atroposelective N-allylic alkylation","authors":"Dayuan Wang , Jiayi Zong , Bowen Wang , Longwu Sun , Xiao Xiao , Huri Piao , Miaolin Ke , Fener Chen","doi":"10.1016/j.gresc.2024.05.006","DOIUrl":"10.1016/j.gresc.2024.05.006","url":null,"abstract":"<div><div>Axially chiral anilide compounds are an emerging but scarcely investigated class of stereogenic molecules with potential applications as chiral catalysts, biologically active scaffolds and functional materials. Compared to the C–C axially chiral molecules, the synthesis of axially chiral anilide compounds is a challenge owing to the lower rotation barriers. Herein, the construction of chiral allylic amine bearing axial chirality and central chirality <em>via</em> Pd-catalyzed atroposelective <em>N</em>-allylic alkylation reaction of cyclic vinyl carbonates and sulfonamides is reported. A diverse range of chiral sulfonamides bearing axial chirality and central chirality were synthesized in high yields and excellent enantioselectivities (up to 92 % yield and 99 % <em>ee</em>). In addition, the practical application of this protocol was also demonstrated by gram-scale synthesis and derivatives of the compound.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 211-215"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141936658","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-05-01Epub Date: 2024-02-06DOI: 10.1016/j.gresc.2024.01.008
Da-Ying Shao, Bin Qiu, Zi-Kang Wang, Zhen-Yuan Liu, Jian Xiao, Xiao-De An
1,7-Hydride transfer-involved dearomatization of quinolines toward C3-spiro hydroquinoline derivatives has been developed. This method offers a protocol to achieve the dearomatization of electron-deficient arenes via the redox-neutral hydride transfer process. A series of C3-spiro hydroquinolines can be provided in moderate to excellent yields (up to 98 %) with good diastereoselectivities. Significant advantages such as high step- and atom-economy, as well as redox-neutral and mild conditions, make it an appealing alternative to achieve the dearomatization of quinolines.
{"title":"1,7-Hydride transfer-involved dearomatization of quinolines to access C3-spiro hydroquinolines","authors":"Da-Ying Shao, Bin Qiu, Zi-Kang Wang, Zhen-Yuan Liu, Jian Xiao, Xiao-De An","doi":"10.1016/j.gresc.2024.01.008","DOIUrl":"10.1016/j.gresc.2024.01.008","url":null,"abstract":"<div><div>1,7-Hydride transfer-involved dearomatization of quinolines toward C3-spiro hydroquinoline derivatives has been developed. This method offers a protocol to achieve the dearomatization of electron-deficient arenes <em>via</em> the redox-neutral hydride transfer process. A series of C3-spiro hydroquinolines can be provided in moderate to excellent yields (up to 98 %) with good diastereoselectivities. Significant advantages such as high step- and atom-economy, as well as redox-neutral and mild conditions, make it an appealing alternative to achieve the dearomatization of quinolines.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 123-127"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139828396","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-05-01Epub Date: 2024-03-08DOI: 10.1016/j.gresc.2024.02.007
Qian Zhou , Lulin Qiao , An-An Zhang , Lu Li , Tuan-Jie Meng , Baomin Fan , Yuan-Yuan Gao , Lantao Liu
Herein, we report an intramolecular 6-endo-dig cyclization of N-ferrocenyl propiolamides for the synthesis of planar chiral ferrocenes enabled by gold(I)-catalyzed hydroarylation. By using this protocol, a variety of planar chiral ferrocenopyridin-2(1H)-ones were obtained in good yields and excellent enantioselectivities (up to 96 % ee).
{"title":"Enantioselective synthesis of planar chiral ferrocenes via gold(I)-catalyzed hydroarylation of N-ferrocenyl propiolamides","authors":"Qian Zhou , Lulin Qiao , An-An Zhang , Lu Li , Tuan-Jie Meng , Baomin Fan , Yuan-Yuan Gao , Lantao Liu","doi":"10.1016/j.gresc.2024.02.007","DOIUrl":"10.1016/j.gresc.2024.02.007","url":null,"abstract":"<div><div>Herein, we report an intramolecular <em>6-endo-dig</em> cyclization of <em>N</em>-ferrocenyl propiolamides for the synthesis of planar chiral ferrocenes enabled by gold(I)-catalyzed hydroarylation. By using this protocol, a variety of planar chiral ferrocenopyridin-2(1<em>H</em>)-ones were obtained in good yields and excellent enantioselectivities (up to 96 % <em>ee</em>).</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 198-201"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140098312","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-05-01Epub Date: 2023-12-18DOI: 10.1016/j.gresc.2023.11.009
Chenhuai Deng , Yuanhao Lin , Yunye Huang , Linxi Hou , Longqiang Xiao
Vesicles obtained by the self-assembly of asymmetric tetrablock copolymers are a class of materials with fascinating properties. However, simple strategies to synthesize asymmetric tetrablock copolymers are limited. Herein, we have designed and synthesized an initiator which generates radicals by either heating or photoirradiation. Taking the advantages of organocatalyzed reversible complexation mediated radical polymerization which has lower energy requirements, milder reaction conditions, and reduced generation of hazardous byproducts, a three steps synthetic route following “photo-photo-thermal” initiation condition for the preparation of asymmetric CABC tetrablock copolymers with controllable molecular weight, precise block composition and low polydispersity was developed.
{"title":"Facile synthesis of asymmetric tetrablock copolymer by dual thermal and photochemical initiator","authors":"Chenhuai Deng , Yuanhao Lin , Yunye Huang , Linxi Hou , Longqiang Xiao","doi":"10.1016/j.gresc.2023.11.009","DOIUrl":"10.1016/j.gresc.2023.11.009","url":null,"abstract":"<div><div>Vesicles obtained by the self-assembly of asymmetric tetrablock copolymers are a class of materials with fascinating properties. However, simple strategies to synthesize asymmetric tetrablock copolymers are limited. Herein, we have designed and synthesized an initiator which generates radicals by either heating or photoirradiation. Taking the advantages of organocatalyzed reversible complexation mediated radical polymerization which has lower energy requirements, milder reaction conditions, and reduced generation of hazardous byproducts, a three steps synthetic route following “photo-photo-thermal” initiation condition for the preparation of asymmetric CABC tetrablock copolymers with controllable molecular weight, precise block composition and low polydispersity was developed.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 164-170"},"PeriodicalIF":0.0,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138744802","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-01DOI: 10.1016/j.gresc.2025.03.005
Lanxue Li, Mengyuan Liu, Yaru Yan, Xiaoqing Liu, Ruyue Dong, Yiwen Shen, Yingguo Bai, Xing Qin, Xiaolu Wang, Huiying Luo, Bin Yao, Xin Jin, Tao Tu
Tartaric acid (TA) is a crucial hydroxy-carboxylic acid chelating agent extensively employed in the pharmaceutical, food, dye, and energy industries. The utilization of glucose oxidation for TA synthesis represents an appealing yet challenging, environmentally-friendly approach. In this study, we developed a two-step chemoenzymatic strategy involving the efficient generation of gluconic acid (GA) through glucose oxidase (Gox) catalysis, followed by chemical decarboxylation to synthesize TA from GA. To optimize the production efficiency of GA and eliminate substrate inhibition in chemocatalysis, we successfully engineered a quadruple variant GoxM10 by implementing rigidifying structure strategies and refining the pH curve. This resulted in a substantial increase in the conversion rate of GA from 45% to 100%, along with improved thermo- and pH stability, as well as enhanced catalytic efficiency. Subsequently, durable bimetallic catalysts were designed for the conversion of Gox-bioconverted GA (bio-GA) to TA. Given the presence of impurities such as acetic acid and sodium acetate in bio-GA, which impacted the selectivity of TA, our focus was on investigating the influence of impurities in bio-GA on the performance of a bimetallic AuPt/TiO 2 catalyst and elucidating an inhibition mechanism that reveals a strong interaction between acetate and Au site, resulting in the formation of a complex compound while promoting uncontrollable C-C cleavage reactions. Through employing a chemoenzymatic two-step strategy, we successfully achieved an environmentally friendly and sustainable route from glucose to TA. This study provides valuable insights into catalyst design and optimization of reaction routes for renewable carboxylic acids and their derivatives synthesized through chemoenzymatic methods. This study utilizes glucose as a substrate and combines durable glucose oxidase with bimetallic catalysts to construct a chemoenzymatic cascade reaction for the green synthesis of tartaric acid.
{"title":"Chemoenzymatic two-step synthesis of tartaric acid employing glucose oxidase in combination with bimetallic AuPt/TiO2 catalyst","authors":"Lanxue Li, Mengyuan Liu, Yaru Yan, Xiaoqing Liu, Ruyue Dong, Yiwen Shen, Yingguo Bai, Xing Qin, Xiaolu Wang, Huiying Luo, Bin Yao, Xin Jin, Tao Tu","doi":"10.1016/j.gresc.2025.03.005","DOIUrl":"https://doi.org/10.1016/j.gresc.2025.03.005","url":null,"abstract":"Tartaric acid (TA) is a crucial hydroxy-carboxylic acid chelating agent extensively employed in the pharmaceutical, food, dye, and energy industries. The utilization of glucose oxidation for TA synthesis represents an appealing yet challenging, environmentally-friendly approach. In this study, we developed a two-step chemoenzymatic strategy involving the efficient generation of gluconic acid (GA) through glucose oxidase (Gox) catalysis, followed by chemical decarboxylation to synthesize TA from GA. To optimize the production efficiency of GA and eliminate substrate inhibition in chemocatalysis, we successfully engineered a quadruple variant GoxM10 by implementing rigidifying structure strategies and refining the pH curve. This resulted in a substantial increase in the conversion rate of GA from 45% to 100%, along with improved thermo- and pH stability, as well as enhanced catalytic efficiency. Subsequently, durable bimetallic catalysts were designed for the conversion of Gox-bioconverted GA (bio-GA) to TA. Given the presence of impurities such as acetic acid and sodium acetate in bio-GA, which impacted the selectivity of TA, our focus was on investigating the influence of impurities in bio-GA on the performance of a bimetallic AuPt/TiO 2 catalyst and elucidating an inhibition mechanism that reveals a strong interaction between acetate and Au site, resulting in the formation of a complex compound while promoting uncontrollable C-C cleavage reactions. Through employing a chemoenzymatic two-step strategy, we successfully achieved an environmentally friendly and sustainable route from glucose to TA. This study provides valuable insights into catalyst design and optimization of reaction routes for renewable carboxylic acids and their derivatives synthesized through chemoenzymatic methods. This study utilizes glucose as a substrate and combines durable glucose oxidase with bimetallic catalysts to construct a chemoenzymatic cascade reaction for the green synthesis of tartaric acid.","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147330671","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01Epub Date: 2023-11-17DOI: 10.1016/j.gresc.2023.11.005
Yi Luo, Lin Dong
Photo-mediated ruthenium-catalyzed para-C−H difluoroalkylation has been disclosed under extremely mild conditions. This photochemical ruthenium catalyst system is characterized by good functional group compatibility without additional photosensitizers at room temperature.
{"title":"Photo-mediated para-selective C(sp2)−H difluoroalkylations","authors":"Yi Luo, Lin Dong","doi":"10.1016/j.gresc.2023.11.005","DOIUrl":"10.1016/j.gresc.2023.11.005","url":null,"abstract":"<div><div>Photo-mediated ruthenium-catalyzed <em>para</em>-C−H difluoroalkylation has been disclosed under extremely mild conditions. This photochemical ruthenium catalyst system is characterized by good functional group compatibility without additional photosensitizers at room temperature.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 91-95"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512297","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01Epub Date: 2023-11-10DOI: 10.1016/j.gresc.2023.11.001
Bin Qiu , Ya-Fei Shi , Xiao-De An , Shu-Kui Guo , Yao-Bin Shen , Jian Xiao
An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines and naphthoxindoles starting from biaryl aldehydes and secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mannich-type cyclization triggered by the dearomatization of indole with subsequent aromatization via β-elimination and then amination or oxidation at the C2-position of the indole nucleus. The secondary amine-controlled divergent protocol together with an easy product isolation process provides a practical route for the first time to access naphtho-fused 2-substituted indoline.
{"title":"Divergent synthesis of new naphtho-fused 2-aminoindolines and naphthoxindoles based on straightforward construction of phenanthrene","authors":"Bin Qiu , Ya-Fei Shi , Xiao-De An , Shu-Kui Guo , Yao-Bin Shen , Jian Xiao","doi":"10.1016/j.gresc.2023.11.001","DOIUrl":"10.1016/j.gresc.2023.11.001","url":null,"abstract":"<div><div>An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines and naphthoxindoles starting from biaryl aldehydes and secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mannich-type cyclization triggered by the dearomatization of indole with subsequent aromatization <em>via β</em>-elimination and then amination or oxidation at the C2-position of the indole nucleus. The secondary amine-controlled divergent protocol together with an easy product isolation process provides a practical route for the first time to access naphtho-fused 2-substituted indoline.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 110-113"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135615603","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A general and practical carboxylation of benzyl alcohols using the air- and moisture-stable Herrmann-Beller palladacycle was developed. With this novel methodology, numerous carboxylated products were constructed and various functional groups were tolerated. More specifically, some prevailing anti-inflammatory drugs, Ibuprofen, Naproxen, Fenoprofen and Flurbiprofen were all successfully synthesized with this novel procedure. Gram scale experiments revealed the industrial potentiality of this procedure. Several interesting control experiments were performed, and the general reaction pathway was proposed.
{"title":"Highly efficient palladacycle-catalyzed carboxylation of benzyl alcohols","authors":"Shaoke Zhang , Yan Zong , Yu Qian , Jishu Zhang , Gen-Qiang Chen , Xumu Zhang","doi":"10.1016/j.gresc.2024.08.005","DOIUrl":"10.1016/j.gresc.2024.08.005","url":null,"abstract":"<div><div>A general and practical carboxylation of benzyl alcohols using the air- and moisture-stable Herrmann-Beller palladacycle was developed. With this novel methodology, numerous carboxylated products were constructed and various functional groups were tolerated. More specifically, some prevailing <em>anti</em>-inflammatory drugs, Ibuprofen, Naproxen, Fenoprofen and Flurbiprofen were all successfully synthesized with this novel procedure. Gram scale experiments revealed the industrial potentiality of this procedure. Several interesting control experiments were performed, and the general reaction pathway was proposed.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 119-122"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507930","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01Epub Date: 2023-12-01DOI: 10.1016/j.gresc.2023.11.011
Feifei Cao , Congyu Gao , Jingxin Zi , Jianfeng Hu , Yong Yang , Wen-Xiong Zhang , Hao Zhang
An intramolecular C–H arylation of ferrocenyl ortho-bromophenyl sulfide and sulfoxide has been developed with a palladium/non-chiral monophosphine ligand. Under mild reaction conditions, a wide range of ferrocene cyclosulfide and ferrocene cyclosulfoxide were obtained in up to 90 % yield. Moreover, planar chiral ferrocene cyclosulfide with enantioselectivities (up to 45 % ee) was synthesized utilizing chiral phosphine ligands. Furthermore, the compound 4a and 6a can be used as novel chemosensors to detect Cu2+ ion.
{"title":"Palladium-catalyzed intramolecular C–H arylation of ferrocenyl-sulfides, sulfoxide and its application in metal ion recognition","authors":"Feifei Cao , Congyu Gao , Jingxin Zi , Jianfeng Hu , Yong Yang , Wen-Xiong Zhang , Hao Zhang","doi":"10.1016/j.gresc.2023.11.011","DOIUrl":"10.1016/j.gresc.2023.11.011","url":null,"abstract":"<div><div>An intramolecular C–H arylation of ferrocenyl <em>ortho</em>-bromophenyl sulfide and sulfoxide has been developed with a palladium/non-chiral monophosphine ligand. Under mild reaction conditions, a wide range of ferrocene cyclosulfide and ferrocene cyclosulfoxide were obtained in up to 90 % yield. Moreover, planar chiral ferrocene cyclosulfide with enantioselectivities (up to 45 % <em>ee</em>) was synthesized utilizing chiral phosphine ligands. Furthermore, the compound <strong>4a</strong> and <strong>6a</strong> can be used as novel chemosensors to detect Cu<sup>2+</sup> ion.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 67-74"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512317","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-02-01Epub Date: 2023-11-17DOI: 10.1016/j.gresc.2023.11.004
Yumei Huo , Beibei Chen , Xiaoyu Ren , Chao Wang , Rupeng Qi , Zhaoqing Xu
The chiral heterobenzylic amines, such as α-alkyl substituted chiral oxadiazole methylamine skeletons are widely present in pesticides and pharmaceuticals, due to their unique biological activities. The enantioselective C(sp3)-H alkylation of heterobenzylic amines is an important strategy for the synthesis of α-alkylate chiral heterobenzylic amines. Herein, we disclose the first example of photoinduced and Cu-catalyzed enantioselective decarboxylative C(sp3)-H alkylation of oxadiazole methylamines.
{"title":"Asymmetric synthesis of chiral heterobenzylic amines via visible-light-induced enantioselective C(sp3)-H alkylation","authors":"Yumei Huo , Beibei Chen , Xiaoyu Ren , Chao Wang , Rupeng Qi , Zhaoqing Xu","doi":"10.1016/j.gresc.2023.11.004","DOIUrl":"10.1016/j.gresc.2023.11.004","url":null,"abstract":"<div><div>The chiral heterobenzylic amines, such as <em>α</em>-alkyl substituted chiral oxadiazole methylamine skeletons are widely present in pesticides and pharmaceuticals, due to their unique biological activities. The enantioselective C(sp<sup>3</sup>)-H alkylation of heterobenzylic amines is an important strategy for the synthesis of <em>α</em>-alkylate chiral heterobenzylic amines. Herein, we disclose the first example of photoinduced and Cu-catalyzed enantioselective decarboxylative C(sp<sup>3</sup>)-H alkylation of oxadiazole methylamines.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 1","pages":"Pages 114-118"},"PeriodicalIF":0.0,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138512302","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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