Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 1, Pages 307-311Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508076
Keywords
aerobic oxygenation; copper catalysis; cyclization; indoles; internal oxidants
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Funding
- National Natural Science Foundation of China [21572194, 21372187]
- Program for Innovative Research Cultivation Team in University of Ministry of Education of China [1337304]
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A concise synthesis of pyrazolo[1,5-a] indole derivatives by copper-catalyzed aerobic oxygenation and cyclization of indoles with oxime acetates is described. This protocol represents an elegant example of N-1, C-2, and C-3 tri-functionalization of indoles in one-pot. Mechanistic studies indicate the reaction proceeds through a radical procedure. Oximes as an internal oxidant have been demonstrated to be a driver to initiate aerobic oxidation, which provides a new oxidative pattern for C-H functionalization even with high atom- and step-economy.
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