Palladium pincer complex-catalyzed allylic stannylation with hexaalkylditin reagents

Org Lett. 2004 May 27;6(11):1829-31. doi: 10.1021/ol049328d.

Abstract

Palladium pincer complex (1)-catalyzed stannylation of allyl chloride, phosphonate, and epoxide substrates (4a-h) could be performed with hexaalkylditin reagents (3) under mild neutral reaction conditions. This catalytic reaction proceeds via palladium(II) intermediates without involvement of allyl-palladium complexes, and therefore the allylstannane product does not interfere with the palladium catalyst. Use of a combined catalytic system (1 + 2) allowed the development of an effective one-pot procedure for allylation of aldehyde and imine electrophiles. [reaction: see text]