Prev. Article Next Article Table of Contents

Communication

Rhodium-Catalyzed Alkyne Hydrothiolation with Aromatic and Aliphatic Thiols

Supporting Info

Changsheng Cao, Lauren R. Fraser, and Jennifer A. Love*

Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada

J. Am. Chem. Soc., 2005, 127 (50), pp 17614–17615

DOI: 10.1021/ja055096h

Publication Date (Web): November 23, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jenlove@chem.ubc.ca

Abstract

Alkyne hydrothiolation is a potentially attractive method for the formation of vinyl sulfides, which are valuable synthetic intermediates. Known methods for hydrothiolation using alkyl thiols are quite limited. We report herein that Tp*Rh(PPh₃)₂ (Tp* = hydrotris(3,5-dimethylpyrazolyl)borate) is a highly active catalyst for alkyne hydrothiolation with alkyl and aryl thiols. Hydrothiolation using alkyl thiols proceeds with excellent regioselectivity, providing convenient access to branched alkyl vinyl sulfides, which are difficult to synthesize by other means. A mixture of regioisomers is obtained when using aryl thiols, with the branched isomer as the major product, opposite that reported for other Rh complexes.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue December 21, 2005
Received July 27, 2005

Recommend & Share

Related Content

Stereoselective Hydrothiolation of Alkynes Catalyzed by Cesium Base: Facile Access to (Z)-1-Alkenyl SulfidesThe Journal of Organic Chemistry
- Stereoselective Hydrothiolation of Alkynes Catalyzed by Cesium Base: Facile Access to (Z)-1-Alkenyl Sulfides
  Azusa Kondoh, Kazuaki Takami, Hideki Yorimitsu, and Koichiro Oshima
  The Journal of Organic Chemistry 2005 70 (16), pp 6468–6473
  Abstract: Treatment of alkyne with alkanethiol in the presence of a catalytic amount of cesium carbonate and a radical inhibitor in DMSO provides the corresponding adduct, (Z)-1-alkenyl alkyl sulfide, in good yield with high selectivity.
  Abstract | Full Text HTML | Hi-Res PDF
Copper-Catalyzed Synthesis of Vinyl SulfidesOrganic Letters
- Copper-Catalyzed Synthesis of Vinyl Sulfides
  Craig G. Bates, Pranorm Saejueng, Michael Q. Doherty, and D. Venkataraman
  Organic Letters 2004 6 (26), pp 5005–5008
  Abstract: We report a method for the synthesis of vinyl sulfides using the soluble copper(I) catalyst [Cu(phen)(PPh₃)₂]NO₃. The desired vinyl sulfides are obtained in good to excellent yields, with retention of stereochemistry. This protocol tolerates a wide ...
  Abstract | Full Text HTML | Hi-Res PDF
Palladium-Catalyzed anti-Hydrothiolation of 1-AlkynylphosphinesOrganic Letters
- Palladium-Catalyzed anti-Hydrothiolation of 1-Alkynylphosphines
  Azusa Kondoh, Hideki Yorimitsu, and Koichiro Oshima
  Organic Letters 2007 9 (7), pp 1383–1385
  Abstract: Treatment of 1-alkynylphosphine with thiol in the presence of a catalytic amount of palladium acetate results in regio- and stereoselective anti-hydrothiolation, yielding the corresponding (Z)-1-phosphino-2-thio-1-alkene.
  Abstract | Full Text HTML | Hi-Res PDF

Communication

Rhodium-Catalyzed Alkyne Hydrothiolation with Aromatic and Aliphatic Thiols

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Stereoselective Hydrothiolation of Alkynes Catalyzed by Cesium Base: Facile Access to (Z)-1-Alkenyl Sulfides

Copper-Catalyzed Synthesis of Vinyl Sulfides

Palladium-Catalyzed anti-Hydrothiolation of 1-Alkynylphosphines

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES