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

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Synthesis of Functionalized Organoboron Compounds Through Copper(I) Catalysis

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Abstract

The borylation substitution of alkyl halides with diboron reagent proceeded in the presence of a copper(I)/Xantphos catalyst and a stoichiometric amount of K(O-t-Bu) base. The borylation proceeded with normal and secondary alkyl chlorides, bromides, and iodides, but alkyl sulfonates did not react. Menthyl halides afforded the corresponding borylation product with excellent diastereoselectivity, whereas optically active (R)-2-bromo-5-phenylpentane gave a racemic product. The reaction with cyclopropylmethyl bromide resulted in ring-opening products, suggesting that the reaction involves a radical-mediated mechanism.

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Authors and Affiliations

  1. Graduate School of Chemical Sciences and Engineering, Frontier Chemistry Center, Hokkaido University, Sapporo, Hokkaido, Japan

    Koji Kubota

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  1. Koji Kubota
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Correspondence to Koji Kubota .

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Kubota, K. (2017). Copper(I)-Catalyzed Direct Boryl Substitution of Unactivated Alkyl Halides. In: Synthesis of Functionalized Organoboron Compounds Through Copper(I) Catalysis. Springer Theses. Springer, Singapore. https://doi.org/10.1007/978-981-10-4935-4_2

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