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Synthesis 2011(23): 3815-3820  
DOI: 10.1055/s-0031-1289304
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Boron Trihalide Mediated Haloallylation of Aryl Aldehydes and Its Application to the Preparation of (E)-1,3-Dienes

Michael P. Quinn, Min-Liang Yao, Li Yong, George W. Kabalka*
Departments of Chemistry and Radiology, The University of Tennessee, Knoxville, TN 37996-1600, USA
Fax: +1(865)9742997; e-Mail: kabalka@utk.edu;
Further Information

Publication History

Received 17 August 2011
Publication Date:
20 October 2011 (online)

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Abstract

In the presence of boron trihalides, aryl aldehydes couple readily with allylmetals to afford haloallylated products. The reactions tolerate a variety of functional groups. Simple aqueous workup of haloallylation reactions, followed by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene, provides a straightforward route to synthetically useful (E)-1,3-dienes. The mild reaction conditions, readily available starting materials, and high stereoselectivity make this two-step (E)-1,3-diene synthesis quite attractive.

Key words

boron trihalide - allylmetal - haloallylation - diene - ste­reoselectivity

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