Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(24), С. 6861 - 6868
Опубликована: Янв. 1, 2022
The present indirect electrochemically mediated radical protocol outperforms the traditional Friedel–Crafts route with a broad substrate scope and functional group tolerance, as well facile gram-scale synthesis without metal contamination.
Язык: Английский
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
Science China Chemistry, Год журнала: 2023, Номер 67(2), С. 450 - 470
Опубликована: Ноя. 3, 2023
Язык: Английский
Процитировано
51
Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(17)
Опубликована: Фев. 24, 2023
Precisely introducing two similar functional groups into bulk chemical alkenes represents a formidable route to complex molecules. Especially, the selective activation of electrophiles is in crucial demand, yet challenging for cross-electrophile-coupling. Herein, we demonstrate redox-mediated electrolysis, which aryl nitriles are both radical precursors and redox-mediators, enables an intermolecular alkene 1,2-diarylation with remarkable regioselectivity, thereby avoiding involvement transition-metal catalysts. This transformation utilizes cyanoarene anions activating various halides (including iodides, bromides, even chlorides) affords adducts up 83 % yield >20 : 1 regioselectivity more than 80 examples, providing feasible approach bibenzyl derivatives.
Язык: Английский
Процитировано
48
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
Chemical Society Reviews, Год журнала: 2023, Номер 53(1), С. 263 - 316
Опубликована: Дек. 7, 2023
The employment of light and/or electricity - alternatively to conventional thermal energy unlocks new reactivity paradigms as tools for chemical substrate activations. This leads the development synthetic reactions and a vast expansion spaces. review summarizes recent developments in photo- electrochemical activation strategies functionalization strong bonds particularly carbon-heteroatom (C-X)
Язык: Английский
Процитировано
43
Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(4), С. 990 - 995
Опубликована: Янв. 1, 2023
A site-selective electrochemical C–H bromination of (hetero)arenes with 2-bromoethan-1-ol by releasing available ethylene oxide and hydrogen through paired electrolysis has been developed.
Язык: Английский
Процитировано
35
Journal of the American Chemical Society, Год журнала: 2023, Номер 145(41), С. 22298 - 22304
Опубликована: Окт. 6, 2023
The cross-electrophile dialkylation of alkenes enables the formation two C(sp
Язык: Английский
Процитировано
34
ACS Catalysis, Год журнала: 2023, Номер 13(18), С. 12238 - 12268
Опубликована: Сен. 1, 2023
Organofluorine compounds have attracted extensive attention in various industrial fields due to their unique chemical and physical properties. Despite increasing demand a wide range of scientific fields, the synthesis organofluorine still faces several problems, such as difficulties handling fluorinating reagents control chemoselectivity. Compared with formation C–F bonds, activation functionalization carbon–fluorine bonds is very important but challenging topic synthetic chemistry. Due properties nickel, Ni-catalyzed defluorinative cross-couplings been greatly developed past few decades powerful strategies for construction fluorinated organic compounds. This Review summarizes advances cross-coupling aryl fluorides, gem-difluorovinyl trifluoromethyl
Язык: Английский
Процитировано
32
Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(33)
Опубликована: Июнь 13, 2023
Abstract The difunctionalization of unsaturated bonds plays a vital role in the enrichment molecular complexity. While various catalytic methods for alkene and alkyne have been developed recent years, hetero‐functionalization introduction two different atoms has less explored. This is mainly due to challenges associated with achieving high chemo‐, regio‐, stereoselectivity, especially when adding similar from same group across bonds. In this study, we describe nickel‐catalyzed, three‐component reductive protocol 14 element hetero‐difunctionalization 1,3‐enynes using electrochemistry. new method mild, selective, general, allowing silyl‐, germanyl‐, stannyl‐alkylation enynes. Various chlorosilanes as well chlorogermans, chlorostannanes can be successfully used combination aryl/alkyl‐substituted primary, secondary, tertiary alkyl bromides electroreductive coupling.
Язык: Английский
Процитировано
31
Green Chemistry, Год журнала: 2023, Номер 25(17), С. 6733 - 6738
Опубликована: Янв. 1, 2023
A metal free, visible-light driven α-C(sp 3 )−H gem-difluoroallylation of glycine derivatives with CF -alkenes and 1,3-enynes is presented under redox-neutral conditions good yields excellent functional group compatibility.
Язык: Английский
Процитировано
29