Journal of Organic Chemistry p. 355 - 360 (1981)
Update date:2022-09-26
Topics:
Maryanoff, Bruce E.
McComsey, David F.
Nortey, Samuel O.
Reactions of bis(trifluoroacetoxy)borane-THF (1) with compounds containing representative organic functional groups were studied to determine the usefulness of 1 as a selective reducing agent.Reducible functionalities were indoles, ketones, aldehydes, imines, and compounds that readily generate carbocations in trifluoroacetic acid.Many functionalities were inert to 1.Epoxides and ortho esters suffered decomposition under the reaction conditions.Olefins and acetylenes were not hydroborated, and carboxylic acids were not reduced by 1.
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