Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 31, Pages 9092-9096Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503549
Keywords
C H activation; cycloaddition; heterocycles; oxidation; synthetic methods
Categories
Funding
- 973 programs [2015CB856600]
- National Natural Science Foundation of China [21425205, 21372084]
- Shanghai Eastern Scholar Program
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An unprecedented strategy for in situ generation of indole-based ortho-quinodimethanes (oQDMs) from 2-methyl-3-alkylmethylindoles by either a metal-free DDQ- or BQ-mediated dehydrogenative process was developed. These oQDMs were trapped by electron-deficient dienophiles to provide a facile approach to synthetically valuable tetrahydrocarbazoles, carbazoles, and hetereoacenes. The salient features of this transformation include direct C(sp(3))-H bond functionalizations, readily available starting materials, metal-free conditions, high efficiency, operational simplicity, and ease of scale-up.
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