Dearomatization of Indoles via Azido Radical Addition and Dioxygen Trapping To Access 2‑Azidoindolin-3-ols

Dearomatization of Indoles via Azido Radical Addition and Dioxygen Trapping To Access 2‑Azidoindolin-3-ols

Efficient copper-catalyzed aerobic oxidative dearomatization of indoles with trimethylsilyl azide (TMSN3) for the synthesis of 2-azidoindolin-3-ols has been developed. Molecular oxygen served as the oxygen-atom source in this transformation. The multicomponent reaction is appreciated by its high sit...

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Veröffentlicht in:Organic letters 2019-08, Vol.21 (16), p.6217-6220
Hauptverfasser: Xu, Meng-Meng, Cao, Wen-Bin, Ding, Rao, Li, Hai-Yan, Xu, Xiao-Ping, Ji, Shun-Jun
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container_end_page 6220
container_issue 16
container_start_page 6217
container_title Organic letters
container_volume 21
creator Xu, Meng-Meng
Cao, Wen-Bin
Ding, Rao
Li, Hai-Yan
Xu, Xiao-Ping
Ji, Shun-Jun
description Efficient copper-catalyzed aerobic oxidative dearomatization of indoles with trimethylsilyl azide (TMSN3) for the synthesis of 2-azidoindolin-3-ols has been developed. Molecular oxygen served as the oxygen-atom source in this transformation. The multicomponent reaction is appreciated by its high site- and diastereoselectivity, broad substrate scope, and mild conditions at room temperature.
doi_str_mv 10.1021/acs.orglett.9b02009
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title Dearomatization of Indoles via Azido Radical Addition and Dioxygen Trapping To Access 2‑Azidoindolin-3-ols
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