Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 42, Pages 22818-22825Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107438
Keywords
amidation; carbonylimidazoles; chemoselectivity; esterification; organocatalysis
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Funding
- Willamette University Beals Family Fund
- Loyola Marymount University
- Loyola Marymount Seaver College
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The use of N-carbonylimidazoles enables catalytic chemodivergent aniline or alcohol acylation with high chemoselectivity and practicality. These acylation reactions show unprecedented levels of chemoselectivity for multiple functional groups and can be operated on a multigram scale.
Chemoselective transformations are a cornerstone of efficient organic synthesis; however, achieving this goal for even simple transformations, such as acylation reactions, is often a challenge. We report that N-carbonylimidazoles enable catalytic chemodivergent aniline or alcohol acylation in the presence of pyridinium ions or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), respectively. Both acylation reactions display high and broad chemoselectivity for the target group. Unprecedented levels of chemoselectivity were observed in the DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N-H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation of the acylimidazole electrophile.
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