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Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides

Hajime Ito* and Koji Kubota

*Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan, Email:

H. Ito, K. Kubota, Org. Lett., 2012, 14, 890-893.

DOI: 10.1021/ol203413w


Borylation of primary and secondary alkyl chlorides, bromides, and iodides with diboron proceeded in the presence of copper(I)/Xantphos as catalyst and a stoichiometric amount of K(O-t-Bu) as base. Menthyl halides afforded the corresponding borylation product with excellent diastereoselectivity, whereas (R)-2-bromo-5-phenylpentane gave a racemic product.

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ID: J54-Y2012-0360