Journal
TETRAHEDRON LETTERS
Volume 48, Issue 33, Pages 5761-5765Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.06.091
Keywords
tertiary bromide; silver oxide; nucleophile; steric hindrance; quaternary
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Silver oxide used in stoichiometric amounts promoted the direct functionalization of tcrt-alkyl bromides and provided the desired adducts in 39-96% isolated yield. Reaction of tert-bromides with carboxylic acids yielded esters, with alcohols and phenols yielded alkyl and aryl ethers, with amines and anilines yielded selectively mono-alkylated amines and anilines, and with a C-nucleophile yielded an all-carbon quaternary hydrocarbon. The method was applied to a sequential alkylation of a primary amine with two different alkyl bromides yielding selectively a tertiary amine with three different substituents in one-pot. (c) 2007 Elsevier Ltd. All rights reserved.
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