Issue 77, 2017

Photoredox catalysis enabled alkylation of alkenyl carboxylic acids with N-(acyloxy)phthalimide via dual decarboxylation

Abstract

A ruthenium based photoredox catalyst in combination with a substoichiometric amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) efficiently catalyzed dual decarboxylative couplings between alkenyl carboxylic acids and N-(acyloxy)phthalimides derived from aliphatic carboxylic acids, delivering alkylated styrene derivatives in a high regio- and stereo-selective manner under mild reaction conditions. Various types of secondary, tertiary, and quaternary aliphatic carboxylic acids as well as α-amino acids can be used as suitable substrates. Mechanistic analysis suggested that the reaction proceeds through a radical mechanism mediated by a Ru(I)/Ru(II) catalytic cycle with DABCO acting both as the base and the co-catalyst for single electron transfer.

Graphical abstract: Photoredox catalysis enabled alkylation of alkenyl carboxylic acids with N-(acyloxy)phthalimide via dual decarboxylation

Supplementary files

Article information

Article type
Communication
Submitted
28 Jul 2017
Accepted
07 Sep 2017
First published
07 Sep 2017

Chem. Commun., 2017,53, 10719-10722

Photoredox catalysis enabled alkylation of alkenyl carboxylic acids with N-(acyloxy)phthalimide via dual decarboxylation

K. Xu, Z. Tan, H. Zhang, J. Liu, S. Zhang and Z. Wang, Chem. Commun., 2017, 53, 10719 DOI: 10.1039/C7CC05910H

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