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Issue 10, 2015
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Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

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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

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Supplementary files

Article information


Submitted
19 Dec 2014
Accepted
16 Jan 2015
First published
03 Feb 2015

This article is Open Access

Org. Biomol. Chem., 2015,13, 2895-2900
Article type
Communication

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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