Gold(I)-catalyzed addition of thiols and thioacids to 3,3-disubstituted cyclopropenes

Richard J Mudd; Paul Young; James Jordan-Hore; Georgina Margaret Rosair; Ai-Lan Lee

doi:10.1021/jo300930c

Gold(I)-catalyzed addition of thiols and thioacids to 3,3-disubstituted cyclopropenes

Richard J Mudd
, Paul Young
, James Jordan-Hore
, Georgina Margaret Rosair
, Ai-Lan Lee

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

58 Citations (Scopus)

Abstract

Gold(I)-catalyzed reactions of thiols, thiophenols, and thioacids with 3,3-disubstituted cyclopropenes occur in a regioselective and chemoselective manner to produce either vinyl thioethers or primary allylic thioesters in good yields. A survey of commonly used gold(I) catalysts shows Echavarren’s cationic gold(I) catalyst to be most tolerant of deactivation by sulfur. A novel digold with bridging thiolate complex is characterized by X-ray crystallography, shedding light on a possible deactivation pathway.

Original language	English
Pages (from-to)	7633-7639
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	77
Issue number	17
DOIs	https://doi.org/10.1021/jo300930c
Publication status	Published - 7 Sept 2012

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title = "Gold(I)-catalyzed addition of thiols and thioacids to 3,3-disubstituted cyclopropenes",

abstract = "Gold(I)-catalyzed reactions of thiols, thiophenols, and thioacids with 3,3-disubstituted cyclopropenes occur in a regioselective and chemoselective manner to produce either vinyl thioethers or primary allylic thioesters in good yields. A survey of commonly used gold(I) catalysts shows Echavarren{\textquoteright}s cationic gold(I) catalyst to be most tolerant of deactivation by sulfur. A novel digold with bridging thiolate complex is characterized by X-ray crystallography, shedding light on a possible deactivation pathway.",

author = "Mudd, \{Richard J\} and Paul Young and James Jordan-Hore and Rosair, \{Georgina Margaret\} and Ai-Lan Lee",

year = "2012",

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doi = "10.1021/jo300930c",

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T1 - Gold(I)-catalyzed addition of thiols and thioacids to 3,3-disubstituted cyclopropenes

AU - Mudd, Richard J

AU - Young, Paul

AU - Jordan-Hore, James

AU - Rosair, Georgina Margaret

AU - Lee, Ai-Lan

PY - 2012/9/7

Y1 - 2012/9/7

N2 - Gold(I)-catalyzed reactions of thiols, thiophenols, and thioacids with 3,3-disubstituted cyclopropenes occur in a regioselective and chemoselective manner to produce either vinyl thioethers or primary allylic thioesters in good yields. A survey of commonly used gold(I) catalysts shows Echavarren’s cationic gold(I) catalyst to be most tolerant of deactivation by sulfur. A novel digold with bridging thiolate complex is characterized by X-ray crystallography, shedding light on a possible deactivation pathway.

AB - Gold(I)-catalyzed reactions of thiols, thiophenols, and thioacids with 3,3-disubstituted cyclopropenes occur in a regioselective and chemoselective manner to produce either vinyl thioethers or primary allylic thioesters in good yields. A survey of commonly used gold(I) catalysts shows Echavarren’s cationic gold(I) catalyst to be most tolerant of deactivation by sulfur. A novel digold with bridging thiolate complex is characterized by X-ray crystallography, shedding light on a possible deactivation pathway.

U2 - 10.1021/jo300930c

DO - 10.1021/jo300930c

M3 - Article

C2 - 22840189

SN - 0022-3263

VL - 77

SP - 7633

EP - 7639

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Gold(I)-catalyzed addition of thiols and thioacids to 3,3-disubstituted cyclopropenes

Abstract

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