Synlett 2005(3): 514-516  
DOI: 10.1055/s-2005-862349
LETTER
© Georg Thieme Verlag Stuttgart · New York

Tunable 1,3-Lithium Shift of Propargylic/Allenylic Lithiums Formed by ­Conjugate Addition of 4-Aryl-3-butyn-1-enes with Organolithiums and the Subsequent Transmetalation/Pd(0)-Catalyzed Coupling Reaction with Aryl Halides

Shengming Ma*, Qiwen He, Xin Jin
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
Fax: +86(21)64167510; e-Mail: masm@mail.sioc.ac.cn;
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Publikationsverlauf

Received 5 November 2004
Publikationsdatum:
17. Januar 2005 (online)

Abstract

A protocol was established to control the 1,3-lithium shift in propargylic/allenylic species formed by the conjugate addition of 4-aryl-3-butyn-1-enes with organolithiums. Subsequent transmetalation and Pd(0)-catalyzed cross-coupling with aryl halides afforded 1,1-diarylallenes and 1,3-diarylallenes, respectively, the structural diversities of which are determined by the easily availability of both 4-aryl-3-butyn-1-enes and the organolithium reagents.

1

There are 22672 allene reactions summarized in Beilstein data.