Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 22, Pages 6467-6470Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602020
Keywords
carbene insertion; density functional calculations; diazo compounds; palladium catalysis; pyrrolidines
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Funding
- MINECO-FEDER [CTQ2012-31391, CTQ2013-44303-P, CTQ2015-64937-R, CTQ2014-51912-REDC]
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A palladium-catalyzed carbene insertion into C(sp(3))-H bonds leading to pyrrolidines was developed. The coupling reaction can be catalyzed by both Pd-0 and Pd-II, is regioselective, and shows a broad functional group tolerance. This reaction is the first example of palladium-catalyzed C(sp(3))-C(sp(3)) bond assembly starting from diazocarbonyl compounds. DFT calculations revealed that this direct C(sp(3))-H bond functionalization reaction involves an unprecedented concerted metalation-deprotonation step.
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