Issue 10, 2015

Chemoselective and fast decarboxylative allylation by photoredox catalysis under mild conditions

Abstract

Here we report a visible-light-induced decarboxylative allylation to build C(sp3)–allyl bonds. This allylation reaction works for primary, secondary, tertiary, benzyl, and alpha-heteroatom-substituted alkyl N-acyloxyphthalimides and is compatible with many sensitive functional groups. The reaction is complete in minutes at room temperature and can be run in both organic solvents and neutral aqueous solutions. A series of mechanistic experiments have been implemented and a functional-group-rich oligosaccharide modification is demonstrated with the decarboxylative allylation.

Graphical abstract: Chemoselective and fast decarboxylative allylation by photoredox catalysis under mild conditions

Supplementary files

Article information

Article type
Research Article
Submitted
12 jun 2015
Accepted
01 ago 2015
First published
03 ago 2015

Org. Chem. Front., 2015,2, 1352-1355

Chemoselective and fast decarboxylative allylation by photoredox catalysis under mild conditions

C. Hu and Y. Chen, Org. Chem. Front., 2015, 2, 1352 DOI: 10.1039/C5QO00187K

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