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  • Chemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions.

Chemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions.

Journal of the American Chemical Society (2017-01-25)
Alberto Osuna Gálvez, Cédric P Schaack, Hidetoshi Noda, Jeffrey W Bode
摘要

Current methods for constructing amide bonds join amines and carboxylic acids by dehydrative couplings-processes that usually require organic solvents, expensive and often dangerous coupling reagents, and masking other functional groups. Here we describe an amide formation using primary amines and potassium acyltrifluoroborates promoted by simple chlorinating agents that proceeds rapidly in water. The reaction is fast at acidic pH and tolerates alcohols, carboxylic acids, and even secondary amines in the substrates. It is applicable to the functionalization of primary amides, sulfonamides, and other N-functional groups that typically resist classical acylations and can be applied to late-stage functionalizations.

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Sigma-Aldrich
Methoxy poly(ethylene glycol) KAT, PEG average Mn 20,000
Sigma-Aldrich
Methoxy poly(ethylene glycol) KAT, PEG average Mn 5,000
Sigma-Aldrich
Methoxy poly(ethylene glycol) KAT, PEG average Mn 10,000
Sigma-Aldrich
Poly(ethylene glycol) bis(2-pyridyl KAT), PEG average Mn 10,000

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