Mild procedure for the catalytic bis(stannylation) of alkynes with hexaalkylditins.
[reaction: see text] Bis(stannylation) of terminal alkynes is achieved through the use of a palladium-isonitrile catalyst complex using a hexaalkylditin as a stannyl group transfer reagent in an atom-efficient and mild catalytic process. Functional group tolerance is good, allowing the presence of amine, carbamate, silyl, ester, and ether moieties. An activated internal alkyne also underwent bis(stannylation) in moderate yield, allowing access to symmetrical bis(alkenyl)stannanes.
Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
John
J
Mancuso
Mark
M
Lautens