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Synthesis of 1,1-Disubstituted Alkyl Vinyl Sulfides via Rhodium-Catalyzed Alkyne Hydrothiolation: Scope and Limitations

TitleSynthesis of 1,1-Disubstituted Alkyl Vinyl Sulfides via Rhodium-Catalyzed Alkyne Hydrothiolation: Scope and Limitations
Publication TypeJournal Article
Year of Publication2009
AuthorsYang, J, Sabarre, A, Fraser, LR, Patrick, BO, Love, JA
JournalJOURNAL OF ORGANIC CHEMISTRY
Volume74
Pagination182-187
Date PublishedJAN 2
ISSN0022-3263
Abstract

Described herein are the scope and limitations using Tp{*}Rh(PPh3)(2) as a catalyst for alkyne hydrothiolation with alkyl thiols. In general, catalytic hydrothiolation proceeds in high yields and with high regioselectivity a wide range of alkynes and thiols. A variety of functional groups were well-tolerated, including intriles, amines, halogens, ethers, esters and silanes, although strongly coordinating groups were found to be incompatible with hydrothiolation. Both sterically encumbered alkynes and thiols were successful in hydrothiolation. Electron rich alkynes react more rapidly than electron deficient alkynes. Overall, this hydrothiolation protocol provides convenient access to a variety of functionalized branched alkyl vinyl sulfides.

DOI10.1021/jo801644s