Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 48, Pages 15436-15440Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709894
Keywords
cascade reactions; copper catalysis; cyclization; nitrogen shift; nitrogen-centered radicals
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Funding
- Chinese Academy of Sciences [XDB20000000]
- National Basic Research Program of China (973 Program) [2015CB856600]
- National Science Foundation of China [21602213, 21522208, 21372209]
- Fundamental Research Funds for the Central Universities [WK2060190046]
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A novel radical [1,3]-nitrogen shift catalyzed by copper diacetate under an oxygen atmosphere (1atm) has been developed for the construction of a diverse range of indole derivatives from ,-disubstituted benzylamine. In this reaction, oxygen was used as a clean terminal oxidant, and water was produced as the only by-product. Five inert bonds were cleaved, and two C-N bonds and one C-C double bond were constructed in one pot during this transformation. This unique method demonstrated broad application protential for the late-stage modification of biologically active natural products and drugs. Mechanistic investigations indicate that a unique 4-exo-trig cyclization of an aminyl radical onto a phenyl ring is involved in the catalytic cycle.
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