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An Efficient Synthesis of Amides and Esters via Triacyloxyboranes

Zhongping Huang*, John E. Reilly, Ronald N. Buckle

*Department of Medicinal Chemistry, Albany Molecular Research Inc., Albany, NY 12212, USA, Email:

Z. Huang, J. R. Reilly, R. N. Buckle, Synlett, 2007, 1026-1030.

DOI: 10.1055/s-2007-973890

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Borane-tetrahydrofuran complex or borane-methyl sulfide complex is used to generate triacyloxyboranes, which can be effectively reacted with various nucleophiles (alkylamines, arylamines, hydrazides, alcohols, phenols) at reflux in toluene to provide the corresponding amides and esters in excellent yield.

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Key Words

triacyloxyboranes, amides, esters, borane-tetrahydrofuran complex, borane-methyl sulfide complex, boranes, selectivity

ID: J60-Y2007-1100