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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, Email:

M. P. Quinn, M.-L. Yao, G. W. Kabalka, Synthesis, 2011, 3815-3820.

DOI: 10.1055/s-0031-1289304

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Aryl aldehydes couple readily with allylmetals to afford haloallylated products in the presence of boron trihalides. 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.

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Key Words

benzyl chlorides, benzyl bromides, allylation, benzylation

ID: J66-Y2011-3420