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Nickel-Catalyzed Regiodivergent Opening of Epoxides with Aryl Halides: Co-Catalysis Controls Regioselectivity

Yang Zhao and Daniel J. Weix*

*Department of Chemistry, University of Rochester, Rochester, New York, United States 14627-0216, Email: daniel.weixrochester.edu

Y. Zhao, D. J. Weix, J. Am. Chem. Soc., 2014, 136, 48-51.

DOI: 10.1021/ja410704d (free Supporting Information)


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Abstract

A bipyridine-ligated nickel mediates the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis results in opening at the less hindered position via an iodohydrin intermediate. Titanocene cocatalysis results in opening at the more hindered position.


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Key Words

arenes, alcohols, zinc


ID: J48-Y2014