Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 18, Pages 8604-8611Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01472
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Funding
- CSIR-New Delhi [ORIGIN-CSC0108]
- AvH Foundation
- CSIR
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The transition-metal-free and temperature-dependent highly selective reaction of arynes with 2H-azirines allowing the synthesis of either N-unsubstituted or N-arylindoles has been developed. At 60 degrees C, arynes generated from 2-(trimethylsilyl)aryl triflates smoothly insert into 2H-azirines to form 2,3-diarylindoles with high selectivity. Interestingly, when the reaction was performed at -10 degrees C, the selectivity was switched to the formation of 1,2,3-triarylindoles in good yields.
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