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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:

D.-Y. Yuan, Y.-Q. Tu, C.-A. Fan, J. Org. Chem., 2008, 73, 7797-7799.

DOI: 10.1021/jo801434b


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