Journal of the American Chemical Society

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

Full Text: HTML

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 ...

Related Articles:

Recyclable polyurea-microencapsulated Pd (0) nanoparticles: An efficient catalyst for hydrogenolysis of epoxides

[Organic Letters, , vol. 5, # 24 p. 4665 - 4668]

1, 2??Diarylethanols by Alternative Regioselective Reductive Ring??Opening of 2, 3??Diaryloxiranes

[Blasio, Nadia Di; Lopardo, Maria Teresa; Lupattelli, Paolo European Journal of Organic Chemistry, 2009 , # 6 p. 938 - 944]

Efficient catalytic racemization of secondary alcohols

[Tetrahedron Letters, , vol. 39, # 31 p. 5545 - 5548]

SN2 Type Hydrolysis of Secondary Alkyl Halides and Sulfonates in Hydrothermal Water

[Chemistry Letters, , vol. 33, # 7 p. 864 - 865]

Hydroboration with pyridine borane at room temperature

[Journal of the American Chemical Society, , vol. 127, # 16 p. 5766 - 5767]

More Articles...