17960-38-2Relevant articles and documents
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Stetter,Schreckenberg
, p. 1461 (1973)
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Ag2CO3-mediated direct functionalization of alkyl nitriles: Facile synthesis of γ-ketonitriles through nitrile alkylation of enol acetates
Cheng, Pi,Wang, Wei,Wang, Lin,Zeng, Jianguo,Reiser, Oliver,Liang, Yun
, p. 1408 - 1412 (2019/05/06)
Direct C(sp3)-H functionalization of alkyl nitriles is a low toxic and facile route to nitrile-containing compounds. In this research, the Ag2CO3-mediated nitrile methylenation of enol acetates is developed to prepare γ-ketonitriles through the direct C(sp3)-H oxidative functionalization of acetonitrile. A radical pathway is proposed, and acetonitrile serves both as solvent and CN-containing radical source.
Light-Driven Vitamin B12-Catalysed Generation of Acyl Radicals from 2-S-Pyridyl Thioesters
Ociepa, Micha?,Baka, Oskar,Narodowiec, Jakub,Gryko, Dorota
, p. 3560 - 3565 (2017/10/24)
Acyl radicals are invaluable intermediates in organic synthesis, however their generation remains challenging. Herein, we present an unprecedented light-driven, cobalt-catalysed method for the generation of acyl radicals from readily available 2-S-pyridyl thioesters. The synthetic potential of this methodology was demonstrated in the Giese-type acylation of activated olefins in the presence of heptamethyl cobyrrinate. This vitamin B12 derivative proved to be the most efficient catalyst in the studied process. The developed method features broad substrate scope (38 examples), good functional group tolerance, and mild reaction conditions. Moreover, it is easily scalable (illustrated on a 20-fold scale-up procedure), enabling its preparative use. Mechanistic studies revealed that the reaction proceeds via a radical pathway with the key steps involving the formation of an acyl-vitamin B12 complex and subsequent photolysis of the Co?C bond. (Figure presented.).
