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Organocatalytic decarboxylative alkylation of N-hydroxy-phthalimide esters enabled by pyridine-boryl radicals

Author:
GaoThese authors contributed equally to this work., Liuzhou, Wang, Guoqiang, Cao, Jia, Yuan, Dandan, Xu, Cheng, Guo, Xuewen, Li, Shuhua
Source:
Chemical communications 2018 v.54 no.82 pp. 11534-11537
ISSN:
1364-548X
Subject:
alkenes, alkylation, carboxylic acids, catalytic activity, decarboxylation, density functional theory, electron transfer, esters, free radicals
Abstract:
The decarboxylative alkylation of N-hydroxyphthalimide (NHPI) based reactive esters with olefins has been achieved via an organocatalytic strategy. Control experiments and density functional theory calculations suggest that these reactions involve a boryl-radical mediated decarboxylation pathway, which is different from the single electron transfer involved in decarboxylative alkylation reactions reported previously. This metal-free decarboxylative alkylation reaction features good functional compatibility, and broad substrate scope illustrated by the transformations of both the alkyl and aryl carboxylic acid derivatives.
Agid:
6168801