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. 2014 Feb 17;20(8):2159-63.
doi: 10.1002/chem.201304111. Epub 2014 Jan 29.

Tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols

Srijit Biswas  1 , Rahul A Watile, Joseph S M Samec
Affiliations

Tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols

Srijit Biswas et al. Chemistry. .

Abstract

An efficient and highly atom-economical tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols has been developed. This one-step procedure has a wide substrate scope with respect to substituents at the α-position of the alcohol. Both aromatic and aliphatic thiols generated the α-sulfenylated carbonyl products in good to excellent yields. A mechanism is proposed in which the reaction proceeds through a Pd-catalyzed regioselective hydrothiolation at the terminal triple bond of the propargyl alcohol followed by an Au-catalyzed 1,2-hydride migration.

Keywords: atom efficiency; gold; palladium; sulfenylated carbonyl; tandem catalysis.

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