Juan Carlos Nieto-Carmona, Maria Quiros, Iván Arribas-Álvarez, Fernando Pérez-Maseda, Marnix van der Kolk, Ana María Martín Castro, Jorge Labrador-Santiago, Elena Buñuel, Diego Jesus Cardenas Morales
We have developed a Ni-catalyzed cyclodimerization of 1,6-allenyenes which affords pentacyclic derivatives containing a [3]-ladderane. Six new carbon-carbon bonds are formed in a single operation which is fully atom-economical. The reaction proceeds with an inexpensive catalyst and shows a broad scope in the alkyne, the allene and the tethering group. A computational and experimental study on the reaction mechanism suggests that this process proceeds by oxidative cyclometallation of the allenyne coordinated to Ni(0) followed by reductive elimination leading to cyclobutenes. Then, two of these molecules are coupled following a related cyclometallation-reductive elimination sequence, the latter being the rate-limiting step.
{"title":"Synthesis of Ladderanes by Nickel-Catalyzed Cyclodimerization of Allenynes: Scope and Mechanism","authors":"Juan Carlos Nieto-Carmona, Maria Quiros, Iván Arribas-Álvarez, Fernando Pérez-Maseda, Marnix van der Kolk, Ana María Martín Castro, Jorge Labrador-Santiago, Elena Buñuel, Diego Jesus Cardenas Morales","doi":"10.1002/adsc.202400676","DOIUrl":"https://doi.org/10.1002/adsc.202400676","url":null,"abstract":"We have developed a Ni-catalyzed cyclodimerization of 1,6-allenyenes which affords pentacyclic derivatives containing a [3]-ladderane. Six new carbon-carbon bonds are formed in a single operation which is fully atom-economical. The reaction proceeds with an inexpensive catalyst and shows a broad scope in the alkyne, the allene and the tethering group. A computational and experimental study on the reaction mechanism suggests that this process proceeds by oxidative cyclometallation of the allenyne coordinated to Ni(0) followed by reductive elimination leading to cyclobutenes. Then, two of these molecules are coupled following a related cyclometallation-reductive elimination sequence, the latter being the rate-limiting step.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141992027","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}
We present a diastereoselective Au/Pd relay catalytic tandem cyclization reaction to produce dearomatic 2-oxa-7-azaspiro[4.5]decane derivatives under mild conditions. This process involves generating furan-derived azadiene from readily available enynamide, followed by a [2 + 4] cycloaddition with Pd-π-allyl dipole decarboxylated from vinyl benzoxazinanone. Our method efficiently constructs the spiro[4.5]decane skeleton, achieving yields ranging from 31-97% and diastereoselectivities from 6:1 dr to >20:1 dr across 34 examples. This research introduces new cycloaddition sites for azadienes as 1,2-dipoles and offers a reliable approach for constructing oxa-azaspiro[4.5]decane frameworks.
我们介绍了一种非对映选择性 Au/Pd 接替催化串联环化反应，可在温和的条件下生成脱芳香族 2-oxa-7-azaspiro[4.5]decane 衍生物。这一过程包括从容易获得的炔酰胺中生成呋喃衍生的氮杂二烯，然后与从乙烯基苯并恶嗪酮中脱羧的钯-π-烯丙基二极进行[2 + 4]环化反应。我们的方法有效地构建了螺[4.5]癸烷骨架，在 34 个实例中实现了 31-97% 的产率和 6:1 dr 到 >20:1 dr 的非对映选择性。这项研究为作为 1,2-二极的氮杂双环[4.5]癸烷骨架引入了新的环加成位点，并提供了一种构建氧杂氮杂双环[4.5]癸烷骨架的可靠方法。
{"title":"Diastereoselective Synthesis of Dearomatic 2-oxa-7-azaspiro[4.5]decane Derivatives through Gold and Palladium Relay Catalytic Tandem Cyclization of Enynamides with Vinyl Benzoxazinanones","authors":"Jiaming Xu, Yanfeng Gao, Xin Gao, Zhiwei Miao","doi":"10.1002/adsc.202400760","DOIUrl":"https://doi.org/10.1002/adsc.202400760","url":null,"abstract":"We present a diastereoselective Au/Pd relay catalytic tandem cyclization reaction to produce dearomatic 2-oxa-7-azaspiro[4.5]decane derivatives under mild conditions. This process involves generating furan-derived azadiene from readily available enynamide, followed by a [2 + 4] cycloaddition with Pd-π-allyl dipole decarboxylated from vinyl benzoxazinanone. Our method efficiently constructs the spiro[4.5]decane skeleton, achieving yields ranging from 31-97% and diastereoselectivities from 6:1 dr to >20:1 dr across 34 examples. This research introduces new cycloaddition sites for azadienes as 1,2-dipoles and offers a reliable approach for constructing oxa-azaspiro[4.5]decane frameworks.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981071","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}
Pavel Sakharov, Alexander Koronatov, Alexander Khlebnikov, Stanislav Petrovskii, Maksim Luginin, Elena Grachova, Mikhail Novikov
Trimethyl phosphite promotes the synthesis 2,4,5-trisubstituted 2H-1,2,3-triazoles. The protocol developed affords a two-step method towards triazoles from available reagents. 3,4-Disubstituted isoxazolones are initially coupled with diazonium tetrafluoroborates. The subsequent reaction is triggered by a single electron transfer from the phosphite to the diazenylisoxazolone under heating or blue LED irradiation at room temperature. The radical anion cascade proceeds via the “ring opening/decarboxylation/cyclization” sequence. The synthesized triazoles show promising fluorescence in the region from 340 nm to 450 nm with a quantum yield up to 81.6%. The emission energy depends slightly on the substituent nature at the triazole carbon atoms. If an electron-donor group is introduced into the N2 substituent of the triazole ring, it results in a bathochromic shift of the luminescence energy.
{"title":"Synthesis of 2-Aryl-2H-1,2,3-triazoles via P(OMe)3-Promoted Intramolecular Transannulation of 4-Diazenylisoxazol-5(4H)-ones","authors":"Pavel Sakharov, Alexander Koronatov, Alexander Khlebnikov, Stanislav Petrovskii, Maksim Luginin, Elena Grachova, Mikhail Novikov","doi":"10.1002/adsc.202400697","DOIUrl":"https://doi.org/10.1002/adsc.202400697","url":null,"abstract":"Trimethyl phosphite promotes the synthesis 2,4,5-trisubstituted 2H-1,2,3-triazoles. The protocol developed affords a two-step method towards triazoles from available reagents. 3,4-Disubstituted isoxazolones are initially coupled with diazonium tetrafluoroborates. The subsequent reaction is triggered by a single electron transfer from the phosphite to the diazenylisoxazolone under heating or blue LED irradiation at room temperature. The radical anion cascade proceeds via the “ring opening/decarboxylation/cyclization” sequence. The synthesized triazoles show promising fluorescence in the region from 340 nm to 450 nm with a quantum yield up to 81.6%. The emission energy depends slightly on the substituent nature at the triazole carbon atoms. If an electron-donor group is introduced into the N2 substituent of the triazole ring, it results in a bathochromic shift of the luminescence energy.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141986687","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}
Qingyu Wang, Lin Cong, Jiyang Guo, Jiajun Wang, Han Xu, Wenhe Zhang, Weidong Liu, Hongli Wei, Song You
(<i>R</i>)-9-(2-hydroxypropyl) adenine ((<i>R</i>)-HPA) is an important intermediate for the synthesis of tenofovir and its prodrugs. Herein, structure-guided rational design of short-chain dehydrogenase LfSDR1 was adopted to improve the catalytic performance for enantioselective synthesis of (<i>R</i>)-HPA at high substrate loading. The crystal structures of LfSDR1 in its apo form as well as in complex with NADPH were solved, which were used for mutagenesis studies and illustration mechanism. Three residues (G92, E141 and V186) were identified as hotspots by structural analysis, and variants V186A/G92V and V186A/G92V/E141L with remarkably improved activity were obtained. By molecular dynamics (MD) simulation of WT and variants, G92V plays a key role in enzyme-substrate interaction in the binding pocket. Whole cells expressing the mutant LfSDR1-V186A/G92V and glucose dehydrogenase BsGDH from <i>Bacillus subtilis</i> were used as the catalyst, and up to 200 g L-1 substrate without cosolvent was completely converted to (R)-HPA with 99.9% ee and a high space-time yield (STY) of 800 g L-1 day-1. This study improves the understanding of the catalytic mechanism of LfSDR and provides a potential biocatalytic strategy for industrial synthesis of (<i>R</i>)-HPA.
{"title":"Structure-Guided Engineering of a Short-Chain Dehydrogenase LfSDR1 for Efficient Biosynthesis of (R)-9-(2-Hydroxypropyl)adenine, the Key Intermediate of Tenofovir","authors":"Qingyu Wang, Lin Cong, Jiyang Guo, Jiajun Wang, Han Xu, Wenhe Zhang, Weidong Liu, Hongli Wei, Song You","doi":"10.1002/adsc.202400752","DOIUrl":"https://doi.org/10.1002/adsc.202400752","url":null,"abstract":"(<i>R</i>)-9-(2-hydroxypropyl) adenine ((<i>R</i>)-HPA) is an important intermediate for the synthesis of tenofovir and its prodrugs. Herein, structure-guided rational design of short-chain dehydrogenase LfSDR1 was adopted to improve the catalytic performance for enantioselective synthesis of (<i>R</i>)-HPA at high substrate loading. The crystal structures of LfSDR1 in its apo form as well as in complex with NADPH were solved, which were used for mutagenesis studies and illustration mechanism. Three residues (G92, E141 and V186) were identified as hotspots by structural analysis, and variants V186A/G92V and V186A/G92V/E141L with remarkably improved activity were obtained. By molecular dynamics (MD) simulation of WT and variants, G92V plays a key role in enzyme-substrate interaction in the binding pocket. Whole cells expressing the mutant LfSDR1-V186A/G92V and glucose dehydrogenase BsGDH from <i>Bacillus subtilis</i> were used as the catalyst, and up to 200 g L-1 substrate without cosolvent was completely converted to (R)-HPA with 99.9% ee and a high space-time yield (STY) of 800 g L-1 day-1. This study improves the understanding of the catalytic mechanism of LfSDR and provides a potential biocatalytic strategy for industrial synthesis of (<i>R</i>)-HPA.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981072","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}
A visible‐light triplet photocatalyst 5‐acetyl‐2‐mercapto‐benzoic acid methyl ester (AcBSH) was developed through introducing acetyl into benzenethiolate to improve the efficiency of intersystem crossing (ISC) and using o‐methoxyformyl to increase the molar extinction coefficient. In the photocatalytic system of AcBSH, the reductive dearomatization of N‐arylformylindoles is achieved to afford the desired indolines in moderate to excellent yields, including both indoles without (1) and with 2‐substituent (2). The 2‐substituent is a steric hindrance for the conjugation between benzoyl and indole moiety, and makes indole 2 and indole 1 exhibit different reduction potentials (Ered) and different triplet energy levels (ΔET). Thereby, two kinds of substrates undergo primarily two photocatalytic pathways: i) successive SET/protonation pathway, which merging photosensitization via triplet‐triplet energy transfer (EnT) and photoinduced SET for substrates 1, and ii) single electron transfer (SET) from the triplet photocatalyst and a concerted hydrogen atom transfer (HAT) process for substrates 2.
{"title":"Two Photocatalytic Pathways for Reductive Dearomatizations of N‐Arylformylindoles by a Visible‐light Triplet Organocatalyst","authors":"Meng-Yue Ma, Yi-Ping Cai, Qin-Hua Song","doi":"10.1002/adsc.202400759","DOIUrl":"https://doi.org/10.1002/adsc.202400759","url":null,"abstract":"A visible‐light triplet photocatalyst 5‐acetyl‐2‐mercapto‐benzoic acid methyl ester (AcBSH) was developed through introducing acetyl into benzenethiolate to improve the efficiency of intersystem crossing (ISC) and using o‐methoxyformyl to increase the molar extinction coefficient. In the photocatalytic system of AcBSH, the reductive dearomatization of N‐arylformylindoles is achieved to afford the desired indolines in moderate to excellent yields, including both indoles without (1) and with 2‐substituent (2). The 2‐substituent is a steric hindrance for the conjugation between benzoyl and indole moiety, and makes indole 2 and indole 1 exhibit different reduction potentials (Ered) and different triplet energy levels (ΔET). Thereby, two kinds of substrates undergo primarily two photocatalytic pathways: i) successive SET/protonation pathway, which merging photosensitization via triplet‐triplet energy transfer (EnT) and photoinduced SET for substrates 1, and ii) single electron transfer (SET) from the triplet photocatalyst and a concerted hydrogen atom transfer (HAT) process for substrates 2.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141986206","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}
Lorena Escot, Sergio Gonzalez-Granda, Daniel Méndez-Sánchez, Yu Wang, Helen Hailes, Ivan Lavandera, Vicente Gotor-Fernández
The combination of a gold(I) N-heterocyclic carbene complex and an ene-reductase (ERED) has made possible the synthesis of enantiopure β,β-disubstituted ketones in a one-pot concurrent approach. The protocol consists of the Meyer-Schuster rearrangement of racemic propargylic tertiary alcohols using [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-[bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2), followed by asymmetric alkene reduction of the α,β-unsaturated ketone intermediate using the Zymomonas mobilis ERED (NCR-ERED). The chemoenzymatic cascade was optimised with a model substrate, where E/Z-isomers both generated the (R)-ketone, which was rationalised using in silico molecular docking experiments. The cascade was then applied towards the production of a series of (R)-4-substituted-alkan-2-ones in enantiopure form in a straightforward manner.
{"title":"β,β-Disubstituted Alkan-2-ones from Propargylic Alcohols Combining a Meyer-Schuster Rearrangement and Asymmetric Alkene Bioreduction","authors":"Lorena Escot, Sergio Gonzalez-Granda, Daniel Méndez-Sánchez, Yu Wang, Helen Hailes, Ivan Lavandera, Vicente Gotor-Fernández","doi":"10.1002/adsc.202400653","DOIUrl":"https://doi.org/10.1002/adsc.202400653","url":null,"abstract":"The combination of a gold(I) N-heterocyclic carbene complex and an ene-reductase (ERED) has made possible the synthesis of enantiopure β,β-disubstituted ketones in a one-pot concurrent approach. The protocol consists of the Meyer-Schuster rearrangement of racemic propargylic tertiary alcohols using [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-[bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2), followed by asymmetric alkene reduction of the α,β-unsaturated ketone intermediate using the Zymomonas mobilis ERED (NCR-ERED). The chemoenzymatic cascade was optimised with a model substrate, where E/Z-isomers both generated the (R)-ketone, which was rationalised using in silico molecular docking experiments. The cascade was then applied towards the production of a series of (R)-4-substituted-alkan-2-ones in enantiopure form in a straightforward manner.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981069","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}
Jeonghyun Min, Sujin Min, Eunjae Chung, Kyeongwon Moon, Hyung Sik Kim, Taejoo Jeong, Amitava Rakshit, Pargat Singh, Jung Su Park, In Su Kim
The front cover picture, provided by Singh, Park, Kim, and co-workers, illustrates the synthetic method for the vicarious-type nucleophilic amination of azine N-oxides and cyclic iminoamides using iminyl anions, readily generated from organic azides under basic conditions. The formation of iminyl anions and site-selective nucleophilic aromatic substitution in this process were supported by a series of mechanistic investigations including DFT calculations. The utility of C2-aminated products was highlighted by the photocatalytic reduction of a N-oxide group and the formation of a five-membered iridacycle. More details can be found in Update by Singh, Park, Kim, and co-workers (J. Min, S. Min, E. Chung, K. Moon, H. S. Kim, T. Jeong, A. Rakshit, P. Singh, J. S. Park, I. S. Kim, Adv. Synth. Catal. 2024, 366, DOI: 10.1002/adsc.202400669)
封面图片由 Singh、Park、Kim 和合作者提供，说明了利用亚氨基阴离子对偶氮 N-氧化物和环状亚氨基酰胺进行邻接型亲核胺化的合成方法，亚氨基阴离子很容易在碱性条件下从有机偶氮化物中生成。包括 DFT 计算在内的一系列机理研究证实了在这一过程中亚胺阴离子的形成和亲核芳香取代的位点选择性。通过光催化还原一个 N-氧化物基团并形成一个五元铱环，凸显了 C2-氨基产物的实用性。更多详情可参见 Singh、Park、Kim 及合作者的最新研究成果（J. Min、S. Min、E. Chung、K. Moon、H. S. Kim、T. Jeong、A. Rakshit、P. Singh、J. S. Park、I. S. Kim，Adv. Synth.Catal.2024, 366, DOI: 10.1002/adsc.202400669)
{"title":"Redox-Neutral Vicarious-Type Nucleophilic Amination of Heterocyclic N-Oxides with Organic Azides.","authors":"Jeonghyun Min, Sujin Min, Eunjae Chung, Kyeongwon Moon, Hyung Sik Kim, Taejoo Jeong, Amitava Rakshit, Pargat Singh, Jung Su Park, In Su Kim","doi":"10.1002/adsc.202400911","DOIUrl":"https://doi.org/10.1002/adsc.202400911","url":null,"abstract":"The front cover picture, provided by Singh, Park, Kim, and co-workers, illustrates the synthetic method for the vicarious-type nucleophilic amination of azine <i>N</i>-oxides and cyclic iminoamides using iminyl anions, readily generated from organic azides under basic conditions. The formation of iminyl anions and site-selective nucleophilic aromatic substitution in this process were supported by a series of mechanistic investigations including DFT calculations. The utility of C2-aminated products was highlighted by the photocatalytic reduction of a <i>N</i>-oxide group and the formation of a five-membered iridacycle. More details can be found in Update by Singh, Park, Kim, and co-workers (J. Min, S. Min, E. Chung, K. Moon, H. S. Kim, T. Jeong, A. Rakshit, P. Singh, J. S. Park, I. S. Kim, <i>Adv. Synth. Catal</i>. <b>2024</b>, <i>366</i>, DOI: 10.1002/adsc.202400669)","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141981070","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}
A squaramide moiety was introduced at the C-4 position of proline to afford an organocatalyst that served as a stereocontrol element to promote the asymmetric Michael addition of cyclic ketones to maleimides. A variety of chiral succinimides were obtained by the conjugate addition in 84-98% yield accompanied by 58-96% enantioselectivity. The results also include an interesting contrast in the facial selectivity observed with cyclohexanones and cycloheptanones, whereas an asymmetric desymmetrization of 4-alkyl cyclohexanones was also achieved using the transformation.
{"title":"Contrasting Facial Selectivity of a Squaramide-Tagged Proline in the Asymmetric Michael Addition of Ketones to Maleimides","authors":"Srinivasan Easwar, Kiran Kumari, Akram G. H. Khan","doi":"10.1002/adsc.202400791","DOIUrl":"https://doi.org/10.1002/adsc.202400791","url":null,"abstract":"A squaramide moiety was introduced at the C-4 position of proline to afford an organocatalyst that served as a stereocontrol element to promote the asymmetric Michael addition of cyclic ketones to maleimides. A variety of chiral succinimides were obtained by the conjugate addition in 84-98% yield accompanied by 58-96% enantioselectivity. The results also include an interesting contrast in the facial selectivity observed with cyclohexanones and cycloheptanones, whereas an asymmetric desymmetrization of 4-alkyl cyclohexanones was also achieved using the transformation.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141986688","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}
The front cover picture shows two of the founders of fluorine chemistry, Carl Wilhelm Scheele and Henri Moissan, and examples of the fluorine-containing compounds reported in the articles that appear in this special issue of Advanced Synthesis & Catalysis. More information about this issue can be found in the Commentary by the Issue Editor, Véronique Gouverneur (V. Gouverneur, Adv. Synth. Catal. 2024, 366, 3404–3404; DOI: 10.1002/adsc.202400881)
{"title":"Front Cover Picture: Fluorine Chemistry: An Outlook to the Future (Adv. Synth. Catal. 16/2024)","authors":"Véronique Gouverneur","doi":"10.1002/adsc.202400916","DOIUrl":"10.1002/adsc.202400916","url":null,"abstract":"<p>The front cover picture shows two of the founders of fluorine chemistry, Carl Wilhelm Scheele and Henri Moissan, and examples of the fluorine-containing compounds reported in the articles that appear in this special issue of <i>Advanced Synthesis & Catalysis</i>. More information about this issue can be found in the Commentary by the Issue Editor, Véronique Gouverneur (V. Gouverneur, <i>Adv. Synth. Catal</i>. <b>2024</b>, <i>366</i>, 3404–3404; DOI: 10.1002/adsc.202400881)\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":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400916","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141986402","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}
We have developed a method for the synthesis of thieno[3,2‐b]furans on the basis of a strategy consisting of a formal [3+2] cycloaddition utilizing the [1,2]‐phospha‐Brook rearrangement and a subsequent Brønsted base‐mediated cyclization. The method streamlines access to a wide range of well‐organized 2,3,5,6‐tetrasubstituted thieno[3,2‐b]furans that are otherwise difficult to synthesize and is also applicable to the syntheses of 2,3,5,6‐tetrasubstituted seleno[3,2‐b]furans.
{"title":"Synthesis of 2,3,5,6‐Tetrasubstituted Thieno[3,2‐b]furans Through Formal [3+2] Cycloaddition Utilizing [1,2]‐Phospha‐Brook Rearrangement / Brønsted Base‐Mediated Cyclization Sequence","authors":"Azusa Kondoh, Kohei Aita, Masahiro Terada","doi":"10.1002/adsc.202400767","DOIUrl":"https://doi.org/10.1002/adsc.202400767","url":null,"abstract":"We have developed a method for the synthesis of thieno[3,2‐b]furans on the basis of a strategy consisting of a formal [3+2] cycloaddition utilizing the [1,2]‐phospha‐Brook rearrangement and a subsequent Brønsted base‐mediated cyclization. The method streamlines access to a wide range of well‐organized 2,3,5,6‐tetrasubstituted thieno[3,2‐b]furans that are otherwise difficult to synthesize and is also applicable to the syntheses of 2,3,5,6‐tetrasubstituted seleno[3,2‐b]furans.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":5.4,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141974060","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}
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