Journal
ORGANIC LETTERS
Volume 14, Issue 3, Pages 890-893Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol203413w
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- Japan Society for the Promotion of Science (JSPS) [G002]
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Borylation of alkyl halides with diboron proceeded in the presence of a copper(I)/Xantphos catalyst and a stoichiometric amount of K(O-t-Bu) base. The boryl substitution 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 (R)-2-bromo-5-phenylpentane gave a racemic product. Reaction with cyclopropylmethyl bromide resulted in ring-opening products, suggesting the reaction involves a radical pathway.
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