Arylation and Vinylation of Alkenes Based on Unusual Sequential Semipinacol Rearrangement/Grob Fragmentation of Allylic Alcohols
Dao-Yi Yuan, Yong-Qiang Tu* and Chun-An Fan
*State Key Laboratory of Applied Organic Chemistry and
Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China, Email:
tuyq
lzu.edu.cn
D.-Y. Yuan, Y.-Q. Tu, C.-A. Fan, J. Org. Chem., 2008, 73, 7797-7799.
DOI: 10.1021/jo801434b
Abstract
A stereoselective arylation and vinylation of alkenes without transition-metal catalysts takes place through an interesting NBS-promoted semipinacol rearrangement under mild conditions and a subsequent unusual NaOH-mediated Grob fragmentation.
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Key Words
Pinacol Rearrangement, Grob Fragmentation, Styrenes, Dienes, NBS
ID: J42-Y2008-2810
