Issue 92, 2018

An efficient method for retro-Claisen-type C–C bond cleavage of diketones with tropylium catalyst

Abstract

The retro-Claisen reaction is frequently used in organic synthesis to access ester derivatives from 1,3-dicarbonyl precursors. The C–C bond cleavage in this reaction is usually promoted by a number of transition-metal Lewis acid catalysts or organic Brønsted acids/bases. Herein we report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro-Claisen-type reactions. Using this method, a range of synthetically valuable substances can be accessed via solvolysis of 1,3-dicarbonyl compounds.

Graphical abstract: An efficient method for retro-Claisen-type C–C bond cleavage of diketones with tropylium catalyst

Supplementary files

Article information

Article type
Communication
Submitted
10 Sept. 2018
Accepted
19 Okt. 2018
First published
19 Okt. 2018

Chem. Commun., 2018,54, 12970-12973

An efficient method for retro-Claisen-type C–C bond cleavage of diketones with tropylium catalyst

M. A. Hussein, V. T. Huynh, R. Hommelsheim, R. M. Koenigs and T. V. Nguyen, Chem. Commun., 2018, 54, 12970 DOI: 10.1039/C8CC07329E

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