Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 48, Pages 15129-15132Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201607856
Keywords
aliphatic amides; cross-coupling; esterification; homogeneous catalysis; nickel
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Funding
- NIH-NIGMS [R01 GM117016]
- Dreyfus Foundation
- UCLA Gold Shield Alumnae
- University of California, Los Angeles
- Bristol-Myers Squibb
- Foote Family
- Majeti-Alapati family
- University of California, Los Angeles Graduate Division
- National Science Foundation [DGE-1144087]
- NSF [CHE-1048804]
- National Center for Research Resources [S10RR025631]
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Recent studies have demonstrated that amides can be used in nickel-catalyzed reactions that lead to cleavage of the amide C-N bond, with formation of a C-C or C-heteroatom bond. However, the general scope of these methodologies has been restricted to amides where the carbonyl is directly attached to an arene or heteroarene. We now report the nickel-catalyzed esterification of amides derived from aliphatic carboxylic acids. The transformation requires only a slight excess of the alcohol nucleophile and is tolerant of heterocycles, substrates with epimerizable stereocenters, and sterically congested coupling partners. Moreover, a series of amide competition experiments establish selectivity principles that will aid future synthetic design. These studies overcome a critical limitation of current Ni-catalyzed amide couplings and are expected to further stimulate the use of amides as synthetic building blocks in C-N bond cleavage processes.
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