Meiling Wang, Tao Li, Jing Shi, Xiaoqiang Sun, Ke Yang, Zhengyi Li
Heterocyclic compounds are not only ubiquitous in natural products, pharmaceuticals, and organic materials, but also function as essential ligands in both organic and medical chemistry. Among the current synthetic strategies, organocatalysis has garnered considerable attention in recent years owing to its cost-effectiveness, high catalytic efficiency, and environmental sustainability. In the realm of heterocycle synthesis via organocatalysis, calix[4]arenes have emerged as prominent catalysts. This review aims to highlight significant advancements in the calix[4]arene-catalyzed synthesis of five- and six-membered heterocyclic compounds using organic small molecules as starting materials over the past decade.
{"title":"Recent Advances in Calix[4]arene-Catalyzed Synthesis of Five- and Six-Membered Oxa- and Azacycles","authors":"Meiling Wang, Tao Li, Jing Shi, Xiaoqiang Sun, Ke Yang, Zhengyi Li","doi":"10.1002/ejoc.202401461","DOIUrl":"https://doi.org/10.1002/ejoc.202401461","url":null,"abstract":"Heterocyclic compounds are not only ubiquitous in natural products, pharmaceuticals, and organic materials, but also function as essential ligands in both organic and medical chemistry. Among the current synthetic strategies, organocatalysis has garnered considerable attention in recent years owing to its cost-effectiveness, high catalytic efficiency, and environmental sustainability. In the realm of heterocycle synthesis via organocatalysis, calix[4]arenes have emerged as prominent catalysts. This review aims to highlight significant advancements in the calix[4]arene-catalyzed synthesis of five- and six-membered heterocyclic compounds using organic small molecules as starting materials over the past decade.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143393805","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dina Scarpi, Samuele Visi, Ernesto Giovanni Occhiato
The electrophilic α-hydrazination (generally referred to as α-amination) of carbonyl compounds with dialkyl azodicarboxylates is a powerful approach for the preparation of synthetically useful intermediates such as α-amino aldehydes and ketones, α-amino acids, and β-amino alcohols. Many methods for the enantioselective α-hydrazination have been published in the past and many new approaches have been disclosed in the last decade that deal with previously unresolved issues such as the direct enantioselective α-hydrazination of α-branched ketones. The enantioselective α-hydrazination is the field where most significant advances have been attained thanks to new approaches, catalysts and techniques. With this review we intend to cover the literature that appeared between 2015 and 2024. We will classify the various methods according to the strategies for the enantioselective formation of the new C-N bond, mainly based on the formation of chiral enamines, enols and enolates. Miscellaneous methods are grouped at the end of the review. Where relevant, the application of α-hydrazino carbonyl compounds to the synthesis of target molecules will also be illustrated.
{"title":"Recent Advances in the α-Hydrazination (α-Amination) of Carbonyl Compounds","authors":"Dina Scarpi, Samuele Visi, Ernesto Giovanni Occhiato","doi":"10.1002/ejoc.202500049","DOIUrl":"https://doi.org/10.1002/ejoc.202500049","url":null,"abstract":"The electrophilic α-hydrazination (generally referred to as α-amination) of carbonyl compounds with dialkyl azodicarboxylates is a powerful approach for the preparation of synthetically useful intermediates such as α-amino aldehydes and ketones, α-amino acids, and β-amino alcohols. Many methods for the enantioselective α-hydrazination have been published in the past and many new approaches have been disclosed in the last decade that deal with previously unresolved issues such as the direct enantioselective α-hydrazination of α-branched ketones. The enantioselective α-hydrazination is the field where most significant advances have been attained thanks to new approaches, catalysts and techniques. With this review we intend to cover the literature that appeared between 2015 and 2024. We will classify the various methods according to the strategies for the enantioselective formation of the new C-N bond, mainly based on the formation of chiral enamines, enols and enolates. Miscellaneous methods are grouped at the end of the review. Where relevant, the application of α-hydrazino carbonyl compounds to the synthesis of target molecules will also be illustrated.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"55 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385880","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alkynyl sulfides, a significant class of heteroatom‐substituted alkynes, have garnered considerable attention within the synthetic community because of their distinctive characteristics, such as the enhanced reactivity, precise selectivity control, and facile derivatization via C‐S bond couplings. Their transformations can provide a direct access to functionalized organosulfur and even sulfur‐free compounds in a highly regio‐ and stereoselective manner, which is very attractive for many fields, including organic synthesis, material science, medicinal chemistry, and life science. This review summarizes the recent progresses on catalytic reactions of alkynyl sulfides, such as the transition‐metal‐catalyzed controllable functionalizations, including hydro‐, hetero‐, and carbofunctionalizations, electrophilic additions, radical addition‐initiated functionalizations, and formal [2+n] cycloadditions, in which the reaction mechanism, selectivity control, scope and limitations are discussed in detail. Given the rapidly increasing interests and applications of sulfur‐containing compounds in both chemistry and life science, it can be anticipated that this review will be valuable for synthetic chemists and may contribute further development of the alkynyl sulfide chemistry.
{"title":"Catalytic Reactions of Alkynyl Sulfides: Versatile Tools in Synthetic Chemistry","authors":"Gangguo Zhu, Wenkui Lu, Yao Yuan, Rong Jia","doi":"10.1002/ejoc.202401475","DOIUrl":"https://doi.org/10.1002/ejoc.202401475","url":null,"abstract":"Alkynyl sulfides, a significant class of heteroatom‐substituted alkynes, have garnered considerable attention within the synthetic community because of their distinctive characteristics, such as the enhanced reactivity, precise selectivity control, and facile derivatization via C‐S bond couplings. Their transformations can provide a direct access to functionalized organosulfur and even sulfur‐free compounds in a highly regio‐ and stereoselective manner, which is very attractive for many fields, including organic synthesis, material science, medicinal chemistry, and life science. This review summarizes the recent progresses on catalytic reactions of alkynyl sulfides, such as the transition‐metal‐catalyzed controllable functionalizations, including hydro‐, hetero‐, and carbofunctionalizations, electrophilic additions, radical addition‐initiated functionalizations, and formal [2+n] cycloadditions, in which the reaction mechanism, selectivity control, scope and limitations are discussed in detail. Given the rapidly increasing interests and applications of sulfur‐containing compounds in both chemistry and life science, it can be anticipated that this review will be valuable for synthetic chemists and may contribute further development of the alkynyl sulfide chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385092","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ki F. Finch, Alex McSkimming, Xiaodong Zhang, Qi Zhao, Mingshu Xie, Robert A. Pascal
When 8‐bromo‐1,2,3,4,5,6,7‐heptaphenyl‐1,4‐dihydro‐1,4‐epoxynaphthalene (5) is heated with copper powder and no solvent at 340 °C under argon, the chief product is 1,8‐dibenzoyl‐2,3,4,5,6,7,9,10‐octaphenylphenanthrene (6) in yields as high as 68%. The reaction appears to involve Ullmann coupling of 5 and expulsion of two molecules of diphenylacetylene to give a decaphenyl bis(isobenzofuran) which then undergoes intramolecular cyclization and fragmentation to yield phenanthrene 6.
{"title":"One‐Step Formation of a Decasubstituted Phenanthrene by Coupling and Fragmentation of a Smaller Precursor","authors":"Ki F. Finch, Alex McSkimming, Xiaodong Zhang, Qi Zhao, Mingshu Xie, Robert A. Pascal","doi":"10.1002/ejoc.202401326","DOIUrl":"https://doi.org/10.1002/ejoc.202401326","url":null,"abstract":"When 8‐bromo‐1,2,3,4,5,6,7‐heptaphenyl‐1,4‐dihydro‐1,4‐epoxynaphthalene (5) is heated with copper powder and no solvent at 340 °C under argon, the chief product is 1,8‐dibenzoyl‐2,3,4,5,6,7,9,10‐octaphenylphenanthrene (6) in yields as high as 68%. The reaction appears to involve Ullmann coupling of 5 and expulsion of two molecules of diphenylacetylene to give a decaphenyl bis(isobenzofuran) which then undergoes intramolecular cyclization and fragmentation to yield phenanthrene 6.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143393259","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Christina Schøttler, Célia Noël, Laura Le Bras, Hayley Melville, Olivier Alévêque, Arthur H. G. David, Olivier Segut, Maxime Rémond, Eric Levillain, Philippe Blanchard, Mogens Brøndsted Nielsen
Here, we present a series of acceptor‐donor‐acceptor (A‐D‐A) conjugated molecules incorporating an indacenodithiophene‐extended tetrathiafulvalene (IDT‐TTF) as the central electron‐donating moiety, functionalized with various lateral electron acceptors. A key synthetic step was the Vilsmeier‐Haack formylation of the IDT‐TTF, providing the dialdehyde in quantitative yield. This compound was further used for the incorporation of dicyanovinyl and indanedione acceptors. UV‐vis absorption spectroscopy of the A‐D‐A compounds in solution revealed a broad absorption in the visible spectrum which is further red‐shifted when proceeding from solutions to thin films. Their cyclic voltammograms in solution showed a multi‐redox behavior – undergoing both oxidation and reduction events. Notably, the oxidation of these compounds unveiled the formation of intermolecular mixed‐valence and π‐dimer species, especially strong in the case of the indanedione‐containing derivative. Computational calculations helped us to identify the electronic transitions involved in the main absorption bands of these A‐D‐A compounds displaying different behaviors depending on the acceptor attached to the IDT‐TTF core. Finally, the potential of these compounds as donors in organic solar cells was investigated and the best performing solar cell exhibited a modest yet promising power conversion efficiency of 0.87%.
{"title":"Acceptor‐Donor‐Acceptor Systems Based on Indacenodithiophene‐Extended Tetrathiafulvalene","authors":"Christina Schøttler, Célia Noël, Laura Le Bras, Hayley Melville, Olivier Alévêque, Arthur H. G. David, Olivier Segut, Maxime Rémond, Eric Levillain, Philippe Blanchard, Mogens Brøndsted Nielsen","doi":"10.1002/ejoc.202401413","DOIUrl":"https://doi.org/10.1002/ejoc.202401413","url":null,"abstract":"Here, we present a series of acceptor‐donor‐acceptor (A‐D‐A) conjugated molecules incorporating an indacenodithiophene‐extended tetrathiafulvalene (IDT‐TTF) as the central electron‐donating moiety, functionalized with various lateral electron acceptors. A key synthetic step was the Vilsmeier‐Haack formylation of the IDT‐TTF, providing the dialdehyde in quantitative yield. This compound was further used for the incorporation of dicyanovinyl and indanedione acceptors. UV‐vis absorption spectroscopy of the A‐D‐A compounds in solution revealed a broad absorption in the visible spectrum which is further red‐shifted when proceeding from solutions to thin films. Their cyclic voltammograms in solution showed a multi‐redox behavior – undergoing both oxidation and reduction events. Notably, the oxidation of these compounds unveiled the formation of intermolecular mixed‐valence and π‐dimer species, especially strong in the case of the indanedione‐containing derivative. Computational calculations helped us to identify the electronic transitions involved in the main absorption bands of these A‐D‐A compounds displaying different behaviors depending on the acceptor attached to the IDT‐TTF core. Finally, the potential of these compounds as donors in organic solar cells was investigated and the best performing solar cell exhibited a modest yet promising power conversion efficiency of 0.87%.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"69 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385091","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Long‐Jin Zhong , Xuan Shang , Hui Chen , Rui‐Xin Liu , Ke‐Wen Tang , Quan Zhou , Yu Liu
A three‐component alkylsulfonylation/cyclization/hydrolysis relay reaction of 1‐acryloyl‐2‐cyanoindoles with 4‐alkyl Hantzsch esters and Na2S2O5 involving sulfur dioxide insertion has been established to access a series of alkylsulfonyl pyrrolo[1,2‐a]indolediones derivatives. With this method, a variety of primary and secondary alkyl radicals can be used for trapping sulfur dioxide and the corresponding alkylsulfonyl radical intermediates formed in situ, followed by alkyl sulfonyl radical addition, cyclization and hydrolysis. This reaction involves selective cleavage of a carbon‐carbon bond followed by successive formation of three new chemical bonds, in which the cyano group has dual roles as a radical acceptor and a carbonyl source.
{"title":"Three‐Component Alkylsulfonylation of 1‐Acryloyl‐2‐Cyanoindoles with Hantzsch Esters through Sulfur Dioxide Insertion","authors":"Long‐Jin Zhong , Xuan Shang , Hui Chen , Rui‐Xin Liu , Ke‐Wen Tang , Quan Zhou , Yu Liu","doi":"10.1002/ejoc.202401211","DOIUrl":"10.1002/ejoc.202401211","url":null,"abstract":"<div><div>A three‐component alkylsulfonylation/cyclization/hydrolysis relay reaction of 1‐acryloyl‐2‐cyanoindoles with 4‐alkyl Hantzsch esters and Na<sub>2</sub>S<sub>2</sub>O<sub>5</sub> involving sulfur dioxide insertion has been established to access a series of alkylsulfonyl pyrrolo[1,2‐<em>a</em>]indolediones derivatives. With this method, a variety of primary and secondary alkyl radicals can be used for trapping sulfur dioxide and the corresponding alkylsulfonyl radical intermediates formed in situ, followed by alkyl sulfonyl radical addition, cyclization and hydrolysis. This reaction involves selective cleavage of a carbon‐carbon bond followed by successive formation of three new chemical bonds, in which the cyano group has dual roles as a radical acceptor and a carbonyl source.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401211"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142763729","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xingyu Chen , Wenbo Ma , Tairan Kang , Peng Sun , Xiaoqiang Guo
Benzoisoxazoles, with a distinctive 10‐π‐electron system and significant polarity, readily trigger N−O bond cleavage, enabling multifaceted applications in organic synthesis. Over the past decade, the exponentially increased use of benzoisoxazoles towards the synthesis of highly valuable N‐containing scaffolds, especially N‐heterocycles, has garnered substantial attention. In this review, we summarize recent developments in the transformation of 2,1‐ and 1,2‐benzoisoxazoles since 2015, highlighting the neglected resemblances of these two nitroxy heterocycles. Key processes in the assorted reactions of benzoisoxazoles, including mechanisms, scope, catalyst‐controlled chemodivergence, current limitations, and developmental prospects, are also introduced and discussed.
{"title":"Benzoisoxazoles as Privileged Scaffolds in the Design and Synthesis of N‐containing Molecules: A Recent Update","authors":"Xingyu Chen , Wenbo Ma , Tairan Kang , Peng Sun , Xiaoqiang Guo","doi":"10.1002/ejoc.202401021","DOIUrl":"10.1002/ejoc.202401021","url":null,"abstract":"<div><div>Benzoisoxazoles, with a distinctive 10‐π‐electron system and significant polarity, readily trigger <em>N</em>−O bond cleavage, enabling multifaceted applications in organic synthesis. Over the past decade, the exponentially increased use of benzoisoxazoles towards the synthesis of highly valuable <em>N</em>‐containing scaffolds, especially <em>N</em>‐heterocycles, has garnered substantial attention. In this review, we summarize recent developments in the transformation of 2,1‐ and 1,2‐benzoisoxazoles since 2015, highlighting the neglected resemblances of these two nitroxy heterocycles. Key processes in the assorted reactions of benzoisoxazoles, including mechanisms, scope, catalyst‐controlled chemodivergence, current limitations, and developmental prospects, are also introduced and discussed.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401021"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142763726","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The ambition to relate intrinsic features of chemical data to the underlying chemical reaction networks (CRNs) is not new, but has experienced only modest success. This may partly be attributed to a lack of theoretical groundwork connecting idealized theory to actual experimental data with added complexity. In particular: i) many CRNs have species that cannot be directly observed experimentally; ii) the apparent number of underlying reactions is a function of the resolution of the data; iii) chemical phenomena can change the number of discernable independent processes of the data. In this work, we illustrate the application of the recently introduced concept of data dimension, which quantifies the linearly independent dimensions the system composition in a CRN can change. We perform case studies inspecting the dimensionality of chemical data characterizing CRNs, and outline how it can be used for mechanistic interpretation. In some instances, these extended considerations allow us to directly recover the CRN proposed in the literature without any fitting. This demonstrates that, with incomplete information, important clues about CRN structure can still be recovered. Additionally, our approach detects critical subtleties, preventing important candidate reactions from being discarded in mechanistic studies.
{"title":"Case Studies of Dimensionality in Chemical Data","authors":"Dr. Alex Blokhuis , Dr. Robert Pollice","doi":"10.1002/ejoc.202400949","DOIUrl":"10.1002/ejoc.202400949","url":null,"abstract":"<div><div>The ambition to relate intrinsic features of chemical data to the underlying chemical reaction networks (CRNs) is not new, but has experienced only modest success. This may partly be attributed to a lack of theoretical groundwork connecting idealized theory to actual experimental data with added complexity. In particular: i) many CRNs have species that cannot be directly observed experimentally; ii) the apparent number of underlying reactions is a function of the resolution of the data; iii) chemical phenomena can change the number of discernable independent processes of the data. In this work, we illustrate the application of the recently introduced concept of data dimension, which quantifies the linearly independent dimensions the system composition in a CRN can change. We perform case studies inspecting the dimensionality of chemical data characterizing CRNs, and outline how it can be used for mechanistic interpretation. In some instances, these extended considerations allow us to directly recover the CRN proposed in the literature without any fitting. This demonstrates that, with incomplete information, important clues about CRN structure can still be recovered. Additionally, our approach detects critical subtleties, preventing important candidate reactions from being discarded in mechanistic studies.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202400949"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202400949","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880136","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Paula Fraňová , Peter Šafář , Ján Moncoľ , Ivana Žídeková , Prof. Adam Daïch , Štefan Marchalín
A series of novel optically pure aminoindolizidines featuring fused tetrahydro‐furan, thiophene, or pyrrole ring were synthesized from the proteinogenic L‐glutamic acid as a chiral precursor and a nitrogen atom source. The synthetic sequence employed tricyclic indolizidinols as advanced building blocks, which were prepared on a gram‐scale from bioavailable reagents. Key transformations within the used synthetic sequence included diastereoselective Thompson azidation, Staudinger reduction, Jurjew reaction, and highly diastereoselective catalytic hydrogenation. These steps facilitated the efficient and stereoselective synthesis of the ultimate amino‐ and N‐acetylamino‐indolizidines.
{"title":"Diastereoselective Entry to Novel Aminoindolizidines with Fused Furan, Thiophene, and Pyrrole Ring Starting from L‐Glutamic Acid","authors":"Paula Fraňová , Peter Šafář , Ján Moncoľ , Ivana Žídeková , Prof. Adam Daïch , Štefan Marchalín","doi":"10.1002/ejoc.202401219","DOIUrl":"10.1002/ejoc.202401219","url":null,"abstract":"<div><div>A series of novel optically pure aminoindolizidines featuring fused tetrahydro‐furan, thiophene, or pyrrole ring were synthesized from the proteinogenic <em>L</em>‐glutamic acid as a chiral precursor and a nitrogen atom source. The synthetic sequence employed tricyclic indolizidinols as advanced building blocks, which were prepared on a gram‐scale from bioavailable reagents. Key transformations within the used synthetic sequence included diastereoselective Thompson azidation, Staudinger reduction, Jurjew reaction, and highly diastereoselective catalytic hydrogenation. These steps facilitated the efficient and stereoselective synthesis of the ultimate amino‐ and <em>N</em>‐acetylamino‐indolizidines.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401219"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401219","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142911973","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dr. Fang Wang , Dr. Bin Wang , Qidi Wang , Prof. Dr. Lei Wang
Acyl radical has assumed an eminent position in the synthetic chemistry due to its unique and often highly reactivity. Using aldehyde as acyl radical source does not require the prefunctionalization of substrate. Furthermore, the formation of acyl radical can be achieved through a hydrogen atom transfer (HAT) process. In recent years, photochemical‐, electrochemical‐, and photoelectrochemical‐catalyzed intermolecular HAT from aldehydes have been regarded as mild and sustainable routes to acyl radicals. Herein, we discuss the important advancements in the past 6 years in photo‐, electro‐, and photoelectro‐catalyzed generation of acyl radicals from aldehydes and their applications in organic synthesis. We also highlight the mechanistic insights that have emerged from these transformations.
{"title":"Photochemical‐, Electrochemical‐, and Photoelectrochemical‐ Catalyzed Hydrogen Atom Transfer from Aldehydes to Acyl Radicals and Their Transformations","authors":"Dr. Fang Wang , Dr. Bin Wang , Qidi Wang , Prof. Dr. Lei Wang","doi":"10.1002/ejoc.202401206","DOIUrl":"10.1002/ejoc.202401206","url":null,"abstract":"<div><div>Acyl radical has assumed an eminent position in the synthetic chemistry due to its unique and often highly reactivity. Using aldehyde as acyl radical source does not require the prefunctionalization of substrate. Furthermore, the formation of acyl radical can be achieved through a hydrogen atom transfer (HAT) process. In recent years, photochemical‐, electrochemical‐, and photoelectrochemical‐catalyzed intermolecular HAT from aldehydes have been regarded as mild and sustainable routes to acyl radicals. Herein, we discuss the important advancements in the past 6 years in photo‐, electro‐, and photoelectro‐catalyzed generation of acyl radicals from aldehydes and their applications in organic synthesis. We also highlight the mechanistic insights that have emerged from these transformations.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401206"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805049","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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