Synthesis of allenes by palladium-catalyzed SN2′ reaction of indium organometallics with propargylic esters.

Riveiros, R.; Pérez Sestelo, J.; Sarandeses, L. A.


Synthesis 2007, 3595–3598 (DOI: 10.1055/s-2007-983849).

trigger text
hidden content

Allenes have been efficiently prepared by the reaction of propargylic esters (benzoates, acetates, carbonates) with triorganoindium compounds (R3In) under palladium catalysis, via an SN2’ rearrangement. The reaction proceeds smoothly at room temperature with a variety of aryl-, alkenyl-, and alkynylindium reagents. The yields obtained are high and the regioselectivity is complete both in the case of terminal and nonterminal propargylic esters.