Electrochemical Difunctionalization of Alkenes: Simultaneous Construction of C–Se and C–S Bonds DOI
Yu Zhou, Jun‐Qi Zhang, Hongjun Ren

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5321 - 5328

Опубликована: Апрель 10, 2023

Electrochemical oxidation of alkene difunctionalization with simultaneous construction C-Se and C-S bonds is reported. The products β-selenylethyl dithiocarbamates are obtained CS2, amines, alkenes, diphenyl diselenides in the absence any oxidant or metal. Furthermore, transformation compatible various groups. In preliminary mechanism studies, we propose three possible pathways.

Язык: Английский

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

Synthetic Advantages of Defluorinative C−F Bond Functionalization DOI Creative Commons
Leidy V. Hooker, Jeffrey S. Bandar

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(49)

Опубликована: Авг. 22, 2023

Abstract Much progress has been made in the development of methods to both create compounds that contain C−F bonds and functionalize bonds. As such, are becoming common versatile synthetic functional handles. This review summarizes advantages defluorinative functionalization reactions for small molecule synthesis. The coverage is organized by type carbon framework fluorine attached mono‐ polyfluorinated motifs. main challenges, opportunities advances discussed each class organofluorine. Most text focuses on case studies illustrate how defluorofunctionalization can improve routes targets or properties enable unique mechanisms reactions. broader goal showcase incorporating exploiting design routes, improvement specific advent new methods.

Язык: Английский

Процитировано

60

Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes DOI
Zhongyi Zhang,

Zhong‐Wei Hou,

Hao Chen

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(9), С. 3543 - 3548

Опубликована: Янв. 1, 2023

An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes with 2-bromoethan-1-ol as the brominating reagent has been developed.

Язык: Английский

Процитировано

51

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

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

A review of frustrated Lewis pair enabled monoselective C–F bond activation DOI Creative Commons
Kenneth Lye, Rowan D. Young

Chemical Science, Год журнала: 2024, Номер 15(8), С. 2712 - 2724

Опубликована: Янв. 1, 2024

Frustrated Lewis pair (FLP) bond activation chemistry has greatly developed over the last two decades since seminal report of metal-free reversible hydrogen activation. Recently, FLP systems have been utilized to allow monoselective C-F (at equivalent sites) in polyfluoroalkanes. The problem 'over-defluorination' functionalization polyfluoroalkanes (where multiple fluoro-positions are uncontrollably functionalized) a long-standing chemical fluorocarbon for 80 years. mediated is complementary other solutions address and offers several advantages unique opportunities. This perspective highlights some these opportunities places development into context wider effort overcome 'over-defluorination'.

Язык: Английский

Процитировано

20

State of knowledge in photoredox-catalysed direct difluoromethylation DOI
Jiaxu Feng, Xiaodong Jia,

Shuyue Zhang

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(13), С. 3598 - 3623

Опубликована: Янв. 1, 2022

The combination of visible light photoredox catalysis with direct difluoromethylation has allowed the synthesis a large choice CF 2 H-containing value-added molecules under very mild reaction conditions.

Язык: Английский

Процитировано

65

Visible‐Light Photosynthesis of CHF2/CClF2/CBrF2‐Substituted Ring‐fused Quinazolinones in Dimethyl Carbonate DOI
Qingwen Gui, Fan Teng, Hao Yang

и другие.

Chemistry - An Asian Journal, Год журнала: 2021, Номер 17(1)

Опубликована: Ноя. 26, 2021

With eco-friendly and sustainable CO2 -derived dimethyl carbonate as the sole solvent, visible-light-induced cascade radical reactions have been established a green efficient tool for constructing various CHF2 /CClF2 /CBrF2 -substituted ring-fused quinazolinones.

Язык: Английский

Процитировано

60

Multiple-fold C–F bond functionalization for the synthesis of (hetero)cyclic compounds: fluorine as a detachable chemical handle DOI
Danhua Ge, Xue‐Qiang Chu

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(7), С. 2013 - 2055

Опубликована: Янв. 1, 2022

We highlighted the recent advances in field of multiple-fold C–F bond functionalization for synthesis (hetero)cyclic compounds.

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