Monotrifluoroacetoxyborane-amines: chemoselective reagents for challenging reductive aminations.

Chem Commun (Camb)

Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana, 47907, USA.

Published: October 2022


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Article Abstract

Borane-amines undergo exclusive monoacetoxylation to trifluoroacetoxyborane-amines (TFAB-amines), which serve as chemoselective reagents for direct reductive amination of aldehydes and ketones. TFABNEt has been established as mild and highly selective compared to widely-used NaBHCN and Na(AcO)BH, even at higher temperatures with challenging substrates. A mechanism involving polyaminoborane formed dehydroacetoxylation of TFABNH has been described.

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http://dx.doi.org/10.1039/d2cc04173aDOI Listing

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