Synthesis of Allenes by Palladium-Catalyzed S_N2′ Reaction of Indium Organometallics with Propargylic Esters

Abstract

Allenes have been efficiently prepared by the reaction of propargylic esters (benzoates, acetates, carbonates) with triorganoindium compounds (R₃In) under palladium catalysis, via an S_N2′ 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.

Key words

allenes - indium organometallics - palladium catalysis - propargylic esters - regioselective reactions

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  DPEphos = bis[o-(diphenylphosphino)phenyl] ether.

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12

For general experimental methods, see ref. 8a.

15

Spectroscopic and analytical data for allenes 5-9 in Table [1] have been previously reported in ref. 9. Spectroscopic and analytical data for allenes 10-13 and 15-19 are reported herein.