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Synthesis 2023; 55(21): 3685-3692
DOI: 10.1055/a-2112-2353
DOI: 10.1055/a-2112-2353
special topic
C–H Bond Functionalization of Heterocycles
Visible-Light-Induced Metal-Free Selenation of Tryptamines/3-Substituted Indoles
Generous financial support from Science and Engineering Research Board (SERB) (CRG/2021/006502) and Department of Atomic Energy, Government of India (201804BRE02RP04978-BRNS.
Abstract
Visible-light-mediated novel metal-free, oxidant-free phosphoric acid-catalyzed method for the synthesis of 2-selanyl NHCbz-tryptamines/3-subtituted indoles is presented. This direct C-2 selenation strategy, with environmental benign conditions by reaction of tryptamines/3-substituted indoles and diaryl/dialkyl selenides, allows access to a wide range of 2-aryl/alkylselanyl NHCbz-tryptamines/3-substituted indoles. An experimental investigation using UV/Vis, cyclic voltammetry, and controlled experiments sheds light on the plausible mechanism.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2112-2353.
- Supporting Information
Publication History
Received: 11 April 2023
Accepted after revision: 19 June 2023
Accepted Manuscript online:
19 June 2023
Article published online:
09 August 2023
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