Substituted 1-Allyl-2-allenylbenzenes via Palladium-Catalyzed Allylallenylation of Benzyne Derivatives

Masilamani Jeganmohan; Chien-Hong Cheng

doi:10.1055/s-2005-869966

SPECIALTOPIC

Substituted 1-Allyl-2-allenylbenzenes via Palladium-Catalyzed Allylallenylation of Benzyne Derivatives

Masilamani Jeganmohan, Chien-Hong Cheng*
Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan
e-Mail: chcheng@mx.nthu.edu.tw;

Abstract

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Abstract

An efficient method for the synthesis of 1-allyl-2-allenyl benzenes via palladium-catalyzed three-component assembly of benzynes, allyl chlorides, and allenylstannanes is described. Substituted benzyne precursors 1a-e undergo three-component assembly with various allylic chlorides 2a-e and allenylstannanes in the presence of Pd(dba)₂/dppe (5 mol%), and cesium fluoride in acetonitrile at ambient temperature affording 1-allyl-2-allenyl benzenes 4a-k in good to excellent yields. The possible mechanism for the present catalytic reaction is proposed.

Key words

1,6-enynes - allylalkylation - palladium - benzyne - allylic chlorides - alkynylstannanes

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References

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