期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 36, 页码 15543-15548出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005066
关键词
DFT calculations; organogermanium; photoredox catalysis
资金
- RWTH Aachen University
- European Research Council
- Alexander von Humboldt Foundation
Selective Csp2-Csp2couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd-0/Pd(II)catalysis) in the presence of the valuable functionalities C-BPin, C-SiMe3, C-I, C-Br, C-Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C-Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar-N-2(+), which were specialized in Ar-N(2)(+)scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar-N(2)(+)salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar-N-2(+), which requires an alternative photo-redox approach to enable productive couplings.
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