Jump to main content
Jump to site search

Issue 77, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Jul 2017, accepted on 07 Sep 2017 and first published on 07 Sep 2017


Article type: Communication
DOI: 10.1039/C7CC05910H
Citation: Chem. Commun., 2017,53, 10719-10722
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements