Synergistic Photoredox and Electrochemical Catalysis in Organic Synthesis and Late‐Stage Functionalizations DOI

Ci‐Yang Sun,

Ting‐Jun Lin,

Yu‐Yu Chen

и другие.

ChemCatChem, Год журнала: 2024, Номер 16(14)

Опубликована: Фев. 7, 2024

Abstract This review delves into the innovative field of interfacial photoelectrochemical (iPEC) and (PEC) catalysis, dynamic synthesis methodologies that seamlessly integrates electrochemical photoredox catalysis for efficient environmentally friendly reactions. Utilizing minute quantities photocatalysts, visible light becomes a powerful tool, generating transient excited states to catalyze spectrum reactions through single‐electron oxidation or reduction events. The categorizes recent advancements, highlighting applications in organic synthesis, late‐stage modifications, distinctive features methodology. Despite being its early stages, this synergistic approach holds great promise propelling forward, with potential large‐scale diverse functionalizations, including asymmetric bioconjugation strategies biomolecule modifications.

Язык: Английский

Electrochemical Late-Stage Functionalization DOI Creative Commons
Yulei Wang, Suman Dana, Hao Long

и другие.

Chemical Reviews, Год журнала: 2023, Номер 123(19), С. 11269 - 11335

Опубликована: Сен. 26, 2023

Late-stage functionalization (LSF) constitutes a powerful strategy for the assembly or diversification of novel molecular entities with improved physicochemical biological activities. LSF can thus greatly accelerate development medicinally relevant compounds, crop protecting agents, and functional materials. Electrochemical synthesis has emerged as an environmentally friendly platform transformation organic compounds. Over past decade, electrochemical late-stage (eLSF) gained major momentum, which is summarized herein up to February 2023.

Язык: Английский

Процитировано

146

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds DOI

Qinhui Wan,

Zhongyi Zhang,

Zhong‐Wei Hou

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(11), С. 2830 - 2848

Опубликована: Янв. 1, 2023

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds and their mechanistic insights synthetic applications have been summarized.

Язык: Английский

Процитировано

80

Electrophilic Halospirocyclization of N-Benzylacrylamides to Access 4-Halomethyl-2-azaspiro[4.5]decanes DOI
Zhongyi Zhang, Wei Zhang,

Zhong‐Wei Hou

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13610 - 13621

Опубликована: Сен. 11, 2023

An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast and efficient route to synthesize wide variety 4-halomethyl-2-azaspiro[4.5]decanes satisfactory yields. The approach further highlighted through gram-scale synthesis diverse transformations spiro products.

Язык: Английский

Процитировано

58

Organoelectrophotocatalytic Generation of Acyl Radicals from Formamides and Aldehydes: Access to Acylated 3-CF3-2-Oxindoles DOI
Hong He,

Qinhui Wan,

Zhong‐Wei Hou

и другие.

Organic Letters, Год журнала: 2023, Номер 25(38), С. 7014 - 7019

Опубликована: Сен. 18, 2023

Organoelectrophotocatalytic generation of acyl radicals from formamides and aldehydes to synthesize acylated 3-CF3-2-oxindoles has been developed. This protocol features a monocatalytic system using 9,10-phenanthrenequinone (PQ) both as catalyst hydrogen atom transfer (HAT) reagent, which avoids the use an external HAT metal oxidant. A variety have obtained in satisfactory yields CF3-substituted N-arylacrylamides via tandem radical cyclization.

Язык: Английский

Процитировано

49

Electrochemically Driven Hydrogen Atom Transfer Catalysis: A Tool for C(sp3)/Si–H Functionalization and Hydrofunctionalization of Alkenes DOI Creative Commons
Sheng Zhang, Michael Findlater

ACS Catalysis, Год журнала: 2023, Номер 13(13), С. 8731 - 8751

Опубликована: Июнь 16, 2023

Electrochemically driven hydrogen atom transfer (HAT) catalysis provides a complementary approach for the transformation of redox-inactive substrates that would be inaccessible to conventional electron (ET) catalysis. Moreover, electrochemically HAT could promote organic transformations with either abstraction or donation as key step. It versatile and effective tool direct functionalization C(sp3)–H/Si–H bonds hydrofunctionalization alkenes. Despite these attractive properties, has been largely overlooked due lack understanding both catalytic mechanism how catalyst selection should occur. In this Review, we give an overview applications in The mechanistic pathways, physical properties mediators, state-of-the-art examples are described discussed.

Язык: Английский

Процитировано

48

Organophotoelectrochemical silylation cyclization for the synthesis of silylated 3-CF3-2-oxindoles DOI

Qinhui Wan,

Chen-Yin Huang,

Zhong‐Wei Hou

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(14), С. 3585 - 3590

Опубликована: Янв. 1, 2023

An organophotoelectrochemical approach for silylation cyclization of CF3-substituted N -arylacrylamides with organosilanes under transition-metal-free and oxidant-free conditions has been developed.

Язык: Английский

Процитировано

44

Organophotoelectrocatalytic C(sp2)–H alkylation of heteroarenes with unactivated C(sp3)–H compounds DOI

Qinhui Wan,

Xia-Die Wu,

Zhong-Wei Hou

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(42), С. 5502 - 5505

Опубликована: Янв. 1, 2024

An organophotoelectrocatalytic method for the C(sp 2 )–H alkylation of heteroarenes with unactivated 3 compounds via dehydrogenation cross-coupling was developed.

Язык: Английский

Процитировано

28

Radical relay cyclization/C–C bond formation of allyloxy-tethered aryl iodides with quinoxalin-2(1H)-ones via polysulfide anion photocatalysis DOI
Zhongyi Zhang, Yaqin Zhou, Jiehui Wang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(8), С. 1708 - 1713

Опубликована: Янв. 1, 2024

A visible-light-induced radical relay cyclization/C-C bond formation of quinoxalin-2(1

Язык: Английский

Процитировано

26

Recent Advances in the Electrochemical Defluorinative Transformations of C—F Bonds DOI

Qinhui Wan,

Ruixue Liu, Zhongyi Zhang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(16), С. 1913 - 1928

Опубликована: Апрель 24, 2024

Comprehensive Summary Organic fluorine compounds are ubiquitous and pivotally important organic molecules, yet their activation transformation have long been a formidable challenge due to the high energy low reactivity of C—F bonds. electrosynthesis, an environmentally benign synthetic method in chemistry, enables myriad chemical transformations without need for external redox reagents. In recent years, electrochemistry has emerged as powerful tool achieving bonds fluorine‐containing compounds. This review aims succinctly recapitulate latest advancements electrochemical defluorinative delve into reaction design, mechanistic insights, developmental prospects these methods. Key Scientists 1959, Lund was first pioneer electroreduction CF 3 CH group. Electrochemistry lately provided new opportunities efficient conversion fluorides. 2020, Zhou coworkers discovered carboxylation α‐CF alkenes. Lambert colleagues reported electrophotocatalytic amination aryl Electrochemical hydrodefluorination trifluoromethylketones developed by Lennox 2021. same year, Wang Guo disclosed radical alkylation alkenes with Katritzky salts alkyl precursors. Subsequently, Wu Liao described transition‐metal‐free, site‐selective arylation polyfluoroarenes (het)arenes using paired electrophotocatalysis. 2023, numerous efforts were made achieve bond activation. Xia organoboron‐controlled chemoselective sequential (deutero)hydrodefluorination trifluoroacetamides.

Язык: Английский

Процитировано

26

Seminormal-BrCH2CH2OH-mediated electrochemical epoxidation of unactivated olefins DOI
Hong He,

Yanxia Lv,

Jing Hu

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(4), С. 2157 - 2161

Опубликована: Янв. 1, 2024

An electrochemical epoxidation of unactivated olefins with water as the source oxygen has been developed.

Язык: Английский

Процитировано

23