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Novel and efficient Ni-mediated pinacol coupling of carbonyl compounds

Lei Shi , Chun-An Fan , Yong-Qiang Tu*, Min Wang and Fu-Min Zhang

*Department of Chemistry and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R., China, Email: tuyqlzu.edu.cn

L. Shi, C.-A. Fan, Y.-Q. Tu, M. Wang, F.-M. Zhang, Tetrahedron, 2004, 60, 2851-2855.

DOI: 10.1016/j.tet.2004.01.073


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Abstract

Rieke Ni generated in situ was able to promote the pinacol coupling of various carbonyls efficiently. Another catalytically effective, cheaper and more convenient NiCl2(Cat.)/Mg/TMSCl system was designed and developed further successfully. Single-electron transfer (SET) mechanisms for the coupling reactions and the DL/meso diastereoselectivity were also explained.

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Key Words

Pinacol Coupling, Nickel, Magnesium

ID: J72-Y2004-230