Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction of Arynes with Azirines

Thangaraj, Manikandan ; Bhojgude, Sachin Suresh ; Jain, Shailja ; Gonnade, Rajesh G. ; Biju, Akkattu T. (2016) Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction of Arynes with Azirines The Journal of Organic Chemistry, 81 (18). pp. 8604-8611. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.6b01472

Related URL: http://dx.doi.org/10.1021/acs.joc.6b01472

Abstract

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 °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 °C, the selectivity was switched to the formation of 1,2,3-triarylindoles in good yields.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128656
Deposited On:03 Nov 2022 06:50
Last Modified:03 Nov 2022 06:50

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