Issue 10, 2015

Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

Abstract

Triazolinylidenes promote γ-selective C-carboxylation (up to 99 : 1 regioselectivity) in the O- to C-carboxyl transfer of furanyl carbonates in contrast to DMAP that promotes preferential α-C-carboxylation with moderate regiocontrol (typically 60 : 40 regioselectivity). The generality of this process is described and a simple mechanistic and kinetic model postulated to account for the observed regioselectivity

Graphical abstract: Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

Supplementary files

Article information

Article type
Communication
Submitted
19 Dec 2014
Accepted
16 Jan 2015
First published
03 Feb 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 2895-2900

Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

C. D. Campbell, C. Joannesse, L. C. Morrill, D. Philp and A. D. Smith, Org. Biomol. Chem., 2015, 13, 2895 DOI: 10.1039/C4OB02629B

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