Journal article
Chemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions.
- Gálvez AO Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich , 8093 Zürich, Switzerland.
- Schaack CP Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich , 8093 Zürich, Switzerland.
- Noda H Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich , 8093 Zürich, Switzerland.
- Bode JW Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich , 8093 Zürich, Switzerland.
- 2017-01-25
Published in:
- Journal of the American Chemical Society. - 2017
English
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.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1021/jacs.7b00059
- PMID 28118000
- Persistent URL
- https://roar.hep-bejune.ch/global/documents/275288
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