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

Craig Donald Campbell; Caroline Joannesse; Louis Christian Morrill; Douglas  Philpa; Andrew David Smith

doi:10.1039/C4OB02629B

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

Craig Donald Campbell
, Caroline Joannesse
, Louis Christian Morrill
, Douglas Philpa
, Andrew David Smith

Research output: Contribution to journal › Article › peer-review

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

Original language	English
Pages (from-to)	2895-2900
Journal	Organic & Biomolecular Chemistry
Volume	13
Issue number	10
Early online date	3 Feb 2015
DOIs	https://doi.org/10.1039/C4OB02629B
Publication status	Published - 14 Mar 2015

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Smith_2015_OBC_Regio_CC
Copyright 2015 the Authors. This open access article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
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title = "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",

author = "Campbell, \{Craig Donald\} and Caroline Joannesse and Morrill, \{Louis Christian\} and Douglas Philpa and Smith, \{Andrew David\}",

note = "The authors would like to thank the Royal Society for a University Research Fellowship (ADS), The Carnegie Trust for the Universities of Scotland (CDC and LCM) and the EPSRC (CJ) for funding, and the EPSRC National Mass Spectrometry Service Centre (Swansea). ",

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doi = "10.1039/C4OB02629B",

language = "English",

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T1 - Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

AU - Campbell, Craig Donald

AU - Joannesse, Caroline

AU - Morrill, Louis Christian

AU - Philpa, Douglas

AU - Smith, Andrew David

N1 - The authors would like to thank the Royal Society for a University Research Fellowship (ADS), The Carnegie Trust for the Universities of Scotland (CDC and LCM) and the EPSRC (CJ) for funding, and the EPSRC National Mass Spectrometry Service Centre (Swansea).

PY - 2015/3/14

Y1 - 2015/3/14

N2 - 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

AB - 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

UR - http://www.rsc.org/suppdata/ob/c4/c4ob02629b/c4ob02629b1.pdf

UR - http://www.rsc.org/suppdata/ob/c4/c4ob02629b/c4ob02629b2.xml

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SN - 1477-0520

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EP - 2900

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 10

ER -

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

Abstract

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