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Synthesis 2020; 52(16): 2395-2409
DOI: 10.1055/s-0040-1707514
DOI: 10.1055/s-0040-1707514
paper
Transition-Metal-Free, Intermolecular Azidoheteroarylation of Alkenes: Efficient Access to β-Azidoalkylated Quinoxalinones and Preliminary Antifungal Evaluation Against Magnaporthe grisea
We gratefully acknowledge the Start-up Grant from South China Agricultural University and Guangdong Basic and Applied Basic Research Foundation 2019 (A1515011824) for the financial support.Further Information
Publication History
Received: 02 March 2020
Accepted after revision: 23 March 2020
Publication Date:
27 April 2020 (online)
Abstract
An efficient, PhI(OAc)2-mediated, radical azidoheteroarylation of alkenes under transition-metal-free conditions is reported by employing TMSN3 and quinoxalin-2(1H)-ones as coupling partners. This domino reaction allows an efficient synthesis of valuable orangoazides containing quinoxalin-2(1H)-one derivatives and could be extended to phosphinyl-alkylated quinoxalin-2(1H)-one in a single step in moderate to excellent yields under mild conditions, as demonstrated by the preliminary antibacterial evaluation against Magnaporthe grisea for the first time. Mechanistic studies revealed that this transformation undergoes a cascade addition pathway controlled by a polar radical.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707514.
- Supporting Information
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