A Highly Regioselective Palladium-Catalyzed O,S Rearrangement of Cyclic Thiocarbonates

William Mahy; Sinéad Cabezas-Hayes; Gabriele Kociok-Köhn; Christopher G. Frost

doi:10.1002/ejoc.201701181

A Highly Regioselective Palladium-Catalyzed O,S Rearrangement of Cyclic Thiocarbonates

William Mahy, Sinéad Cabezas-Hayes, Gabriele Kociok-Köhn, Christopher G. Frost

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

3 Citations (SciVal)

Abstract

This work describes an operationally simple catalytic synthesis of cyclic S-thiocarbonates with predictable regioselectivity in good yields. The reaction utilizes substrates derived from ubiquitous 1,2-diols in an atom economical intramolecular rearrangement, catalysed by an inexpensive and simple catalyst–ligand system. A crystal structure is presented that clearly confirms the regioselectivity of the reaction.

Original language	English
Pages (from-to)	6441-6444
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	43
Early online date	3 Nov 2017
DOIs	https://doi.org/10.1002/ejoc.201701181
Publication status	Published - 24 Nov 2017

Keywords

Alkyl migrations
Homogeneous catalysis
Newman-Kwart
Sulfur
Synthetic methods

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201701181

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keywords = "Alkyl migrations, Homogeneous catalysis, Newman-Kwart, Sulfur, Synthetic methods",

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AU - Mahy, William

AU - Cabezas-Hayes, Sinéad

AU - Kociok-Köhn, Gabriele

AU - Frost, Christopher G.

PY - 2017/11/24

Y1 - 2017/11/24

N2 - This work describes an operationally simple catalytic synthesis of cyclic S-thiocarbonates with predictable regioselectivity in good yields. The reaction utilizes substrates derived from ubiquitous 1,2-diols in an atom economical intramolecular rearrangement, catalysed by an inexpensive and simple catalyst–ligand system. A crystal structure is presented that clearly confirms the regioselectivity of the reaction.

AB - This work describes an operationally simple catalytic synthesis of cyclic S-thiocarbonates with predictable regioselectivity in good yields. The reaction utilizes substrates derived from ubiquitous 1,2-diols in an atom economical intramolecular rearrangement, catalysed by an inexpensive and simple catalyst–ligand system. A crystal structure is presented that clearly confirms the regioselectivity of the reaction.

KW - Alkyl migrations

KW - Homogeneous catalysis

KW - Newman-Kwart

KW - Sulfur

KW - Synthetic methods

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DO - 10.1002/ejoc.201701181

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JF - European Journal of Organic Chemistry

IS - 43

ER -

A Highly Regioselective Palladium-Catalyzed O,S Rearrangement of Cyclic Thiocarbonates

Abstract

Keywords

ASJC Scopus subject areas

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