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Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes

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Abstract

A copper-promoted oxidative cyanomethylation/ring-expansion of vinylcyclopropanes with α-C(sp3)–H bonds in alkyl nitriles is established for the generation of 1-cyanoethylated 3,4-dihydronaphthalenes. This cyanomethylation/ring-expansion involves a radical pathway and proceeds via cyanomethyl radical formation, radical addition and ring-expansion. This ring-expansion strategy offers a highly atom-economical route for the construction of nitrile-containing 3,4-dihydronaphthalenes, which can be transformed into other useful products under simple conditions.

Graphical abstract: Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes

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Article information


Submitted
09 Sep 2020
Accepted
05 Oct 2020
First published
06 Oct 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Copper-promoted cyanoalkylation/ring-expansion of vinylcyclopropanes with α-C–H bonds in alkylnitriles toward 3,4-dihydronaphthalenes

Z. Chen, Q. Zhou, Q. Chen, P. Chen, B. Xiong, Y. Liang, K. Tang, J. Xie and Y. Liu, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB01864C

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