Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 6, Pages 4543-4552Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00018
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Funding
- NSFC [21525208]
- China Postdoctoral Science Foundation [2019TQ0192, 2019M653531, 2019M663613]
- Fundamental Research Funds for the Central Universities [GK201903028]
- SNNU
- National Training Program of Innovation and Entrepreneurship for Undergraduates [CX2019106]
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Reported herein is the Rh(III)-catalyzed annulation of N-unprotected 2-arylindoles with quinone monoacetals for the straightforward synthesis of [4,3,1]-bridged carbocycles with exclusive C(3) selectivity. Mechanistic studies, particularly deuterium-labeling experiments, suggest that the coupling likely proceeds via two-fold C-H activation with two-fold migratory insertion into the enone moieties.
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