Rhodium-catalyzed alkyne hydrothiolation with aromatic and aliphatic thiols.
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.
Cao
Changsheng
C
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada.
Fraser
Lauren R
LR
Love
Jennifer A
JA