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Synthesis 2020; 52(16): 2395-2409
DOI: 10.1055/s-0040-1707514
paper
© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Free, Intermolecular Azidoheteroarylation of Alkenes: Efficient Access to β-Azidoalkylated Quinoxalinones and Preliminary Antifungal Evaluation Against Magnaporthe grisea

Yiming Du
a   Key Laboratory for Biobased Materials and Energy of Ministry of Education and Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: scaulizhaodong@scau.edu.cn   Email: qinweiwei@scau.edu.cn
,
Yue Chen
a   Key Laboratory for Biobased Materials and Energy of Ministry of Education and Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: scaulizhaodong@scau.edu.cn   Email: qinweiwei@scau.edu.cn
,
Yun-Lin Liu 
b   School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, P. R. of China
,
Weiwei Qin∗
a   Key Laboratory for Biobased Materials and Energy of Ministry of Education and Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: scaulizhaodong@scau.edu.cn   Email: qinweiwei@scau.edu.cn
,
Zhaodong Li∗
a   Key Laboratory for Biobased Materials and Energy of Ministry of Education and Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: scaulizhaodong@scau.edu.cn   Email: qinweiwei@scau.edu.cn
c   Key Laboratory of Natural Pesticide & Chemical Biology, Ministry of Education, South China Agricultural University, Guangzhou 510642, P. R. of China
› Author AffiliationsWe 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)

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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.

Key words

radical - domino - difunctionalization - azide - transition-metal-free

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707514.
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