Alkynyl sulfoxides as α-sulfinyl carbene equivalents:: Gold-catalysed oxidative cyclopropanation

Matthew Barrett; Ghulam Khan; Paul Davies; Richard Grainger

doi:10.1039/C7CC02244A

Alkynyl sulfoxides as α-sulfinyl carbene equivalents: Gold-catalysed oxidative cyclopropanation

Matthew Barrett, Ghulam Khan, Paul Davies^*, Richard Grainger^*

^*Corresponding author for this work

Chemistry

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20 Citations (Scopus)

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Abstract

Alkynyl sulfoxides are shown to act as α-sulfinyl metallocarbene synthons under oxidative gold catalysis, enabling reactions that are not available from diazo-precursors. This strategy is exemplified in the synthesis of fused α-sulfinyl cyclopropanes.

Original language	English
Pages (from-to)	5733-5736
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	42
Early online date	4 May 2017
DOIs	https://doi.org/10.1039/C7CC02244A
Publication status	Published - 25 May 2017

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20 Citations
3 Article

Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation
Davies, P., Grainger, R. & Barrett, M., 28 Aug 2015, In: Organic and Biomolecular Chemistry. 13, 32, p. 8676-8686 11 p.
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17 Citations (Scopus)

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A gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides
Santos, M. D. & Davies, P. W., 7 Jun 2014, In: Chemical Communications . 50, 45, p. 6001-6004 4 p.
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66 Citations (Scopus)

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Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers
Davies, P., Cremonesi, A. & Martin, N., 1 Jan 2011, In: Chemical Communications. 47, 1, p. 379-381 3 p.
Research output: Contribution to journal › Article
149 Citations (Scopus)

Birmingham Environment for Academic Research (BEAR)
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title = "Alkynyl sulfoxides as α-sulfinyl carbene equivalents:: Gold-catalysed oxidative cyclopropanation",

abstract = "Alkynyl sulfoxides are shown to act as α-sulfinyl metallocarbene synthons under oxidative gold catalysis, enabling reactions that are not available from diazo-precursors. This strategy is exemplified in the synthesis of fused α-sulfinyl cyclopropanes.",

author = "Matthew Barrett and Ghulam Khan and Paul Davies and Richard Grainger",

year = "2017",

month = may,

day = "25",

doi = "10.1039/C7CC02244A",

language = "English",

volume = "53",

pages = "5733--5736",

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publisher = "Royal Society of Chemistry",

number = "42",

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T1 - Alkynyl sulfoxides as α-sulfinyl carbene equivalents:

T2 - Gold-catalysed oxidative cyclopropanation

AU - Barrett, Matthew

AU - Khan, Ghulam

AU - Davies, Paul

AU - Grainger, Richard

PY - 2017/5/25

Y1 - 2017/5/25

N2 - Alkynyl sulfoxides are shown to act as α-sulfinyl metallocarbene synthons under oxidative gold catalysis, enabling reactions that are not available from diazo-precursors. This strategy is exemplified in the synthesis of fused α-sulfinyl cyclopropanes.

AB - Alkynyl sulfoxides are shown to act as α-sulfinyl metallocarbene synthons under oxidative gold catalysis, enabling reactions that are not available from diazo-precursors. This strategy is exemplified in the synthesis of fused α-sulfinyl cyclopropanes.

U2 - 10.1039/C7CC02244A

DO - 10.1039/C7CC02244A

M3 - Article

SN - 1359-7345

VL - 53

SP - 5733

EP - 5736

JO - Chemical Communications

JF - Chemical Communications

IS - 42

ER -

Alkynyl sulfoxides as α-sulfinyl carbene equivalents: Gold-catalysed oxidative cyclopropanation

Abstract

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Research output

Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

A gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides

Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers

Equipment

Birmingham Environment for Academic Research (BEAR)

Cite this