Nickel-catalyzed regiodivergent opening of epoxides with aryl halides: co-catalysis controls regioselectivity

Y Zhao, DJ Weix

Index: Zhao, Yang; Weix, Daniel J. Journal of the American Chemical Society, 2014 , vol. 136, # 1 p. 48 - 51

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Citation Number: 33

Abstract

Epoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate 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 ...