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Synlett 2005(11): 1789-1793  
DOI: 10.1055/s-2005-871560
CLUSTER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Cross-Coupling of Alkynylzincs with Allylic Electrophiles: An Efficient and Selective Synthesis of Stereo- and Regio-Defined 1,4-Enynes

Mingxing Qian, Ei-ichi Negishi*
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA
e-Mail: negishi@purdue.edu;
Further Information

Publication History

Received 24 February 2005
Publication Date:
28 June 2005 (online)

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Abstract

Clean and high-yielding cross-coupling of alkynylzincs with allylic chlorides, bromides, or acetates exhibiting 98% regio- and stereoselectivity can be achieved by using 1 mol% of ­Pd(DPEphos)Cl2 and either 1:1 THF-DMF or pure DMF. This reaction provides a satisfactory route to 1,4-enynes via Pd-catalyzed alkynyl-allyl coupling.

Key words

Pd-catalyzed alkynyl-allyl coupling - 1,4-enynes - alkynylzincs - allylic electrophiles - Pd(DPEphos)Cl2

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