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

Campbell, Craig D., Joannesse, Caroline, Morrill, Louis ORCID: https://orcid.org/0000-0002-6453-7531, Philp, Douglas and Smith, Andrew D. 2015. Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates. Organic & Biomolecular Chemistry 13 (10) , pp. 2895-2900. 10.1039/C4OB02629B

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Additional Information:	First published online 3 February 2015
Publisher:	Royal Society of Chemistry
ISSN:	1477-0520
Date of Acceptance:	16 January 2015
Last Modified:	28 Oct 2022 09:22
URI:	https://orca.cardiff.ac.uk/id/eprint/74300

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