Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes

Mieko Arisawa; Yui Igarashi; Yoko Tagami; Masahiko Yamaguchi; Chizuko Kabuto

doi:10.1016/j.tetlet.2010.12.065

Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes

Mieko Arisawa, Yui Igarashi, Yoko Tagami, Masahiko Yamaguchi, Chizuko Kabuto

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

24 Citations (Scopus)

Abstract

A rhodium complex derived from RhH(PPh₃)₄ and Me ₂PhP catalyzed the carbothiolation reaction of 1-alkylthio-1-alkynes and 1,4-diaryl-1,3-butadiynes giving (Z)-4-alkylthio-4-aryl-3-arylethynyl-3- buten-1-ynes. Terminal alkynes such as 1-decyne and (t-butylthio)acetylene underwent the carbothiolation reaction using a RhH(PPh₃) ₄-dppb catalyst. The reactions proceeded via cis-addition with C-C bond formation at the less hindered acetylene carbon.

Original language	English
Pages (from-to)	920-922
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2010.12.065
Publication status	Published - Feb 23 2011
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.12.065

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title = "Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes",

abstract = "A rhodium complex derived from RhH(PPh3)4 and Me 2PhP catalyzed the carbothiolation reaction of 1-alkylthio-1-alkynes and 1,4-diaryl-1,3-butadiynes giving (Z)-4-alkylthio-4-aryl-3-arylethynyl-3- buten-1-ynes. Terminal alkynes such as 1-decyne and (t-butylthio)acetylene underwent the carbothiolation reaction using a RhH(PPh3) 4-dppb catalyst. The reactions proceeded via cis-addition with C-C bond formation at the less hindered acetylene carbon.",

author = "Mieko Arisawa and Yui Igarashi and Yoko Tagami and Masahiko Yamaguchi and Chizuko Kabuto",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 21229001), the GCOE program, and the WPI Initiative from JSPS. M.A. expresses her thanks to the Grant-in-Aid for Scientific Research (No. 22689001) and to the Asahi Glass Foundation. ",

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doi = "10.1016/j.tetlet.2010.12.065",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes

AU - Arisawa, Mieko

AU - Igarashi, Yui

AU - Tagami, Yoko

AU - Yamaguchi, Masahiko

AU - Kabuto, Chizuko

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 21229001), the GCOE program, and the WPI Initiative from JSPS. M.A. expresses her thanks to the Grant-in-Aid for Scientific Research (No. 22689001) and to the Asahi Glass Foundation.

PY - 2011/2/23

Y1 - 2011/2/23

N2 - A rhodium complex derived from RhH(PPh3)4 and Me 2PhP catalyzed the carbothiolation reaction of 1-alkylthio-1-alkynes and 1,4-diaryl-1,3-butadiynes giving (Z)-4-alkylthio-4-aryl-3-arylethynyl-3- buten-1-ynes. Terminal alkynes such as 1-decyne and (t-butylthio)acetylene underwent the carbothiolation reaction using a RhH(PPh3) 4-dppb catalyst. The reactions proceeded via cis-addition with C-C bond formation at the less hindered acetylene carbon.

AB - A rhodium complex derived from RhH(PPh3)4 and Me 2PhP catalyzed the carbothiolation reaction of 1-alkylthio-1-alkynes and 1,4-diaryl-1,3-butadiynes giving (Z)-4-alkylthio-4-aryl-3-arylethynyl-3- buten-1-ynes. Terminal alkynes such as 1-decyne and (t-butylthio)acetylene underwent the carbothiolation reaction using a RhH(PPh3) 4-dppb catalyst. The reactions proceeded via cis-addition with C-C bond formation at the less hindered acetylene carbon.

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DO - 10.1016/j.tetlet.2010.12.065

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SN - 0040-4039

VL - 52

SP - 920

EP - 922

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes

Abstract

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