Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 8, Pages 2238-2243Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711209
Keywords
carbenes; cyclopropanation; homogeneous catalysis; nitrogen heterocycles; transannulation
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Funding
- CSIR-EMR-II grant [02(0259)/16/EMR-II]
- Ramanujan grant [SB/S2/RJN-45/2013]
- DST-Young Scientist Grant [SB/FT/CS-141/2014]
- CSIR
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A new catalytic method for the denitrogenative transannulation/cyclopropanation of in-situ-generated 2-(diazomethyl)pyridines is described using a cobalt-catalyzed radical-activation mechanism. The method takes advantage of the inherent properties of a Co-III-carbene radical intermediate and is the first report of denitrogenative transannulation/cyclopropanation by a radical-activation mechanism, which is supported by various control experiments. The synthetic benefits of the metalloradical approach are showcased with a short total synthesis of (+/-)-monomorine.
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