Tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols.
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.
Department of Chemistry, BMC, Uppsala University, Box 576, 75123, Uppsala (Sweden), Fax: (+46) 18 471 38 18.
Srijit
S
Biswas
Rahul A
RA
Watile
Joseph S M
JS
Samec
atom efficiency; gold; palladium; sulfenylated carbonyl; tandem catalysis