Dearomative hydroamination of heteroarenes catalyzed by the phenolate photocatalyst.

Autor: Zhang SR; College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, P. R. China., Yue JP; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. jhye@scu.edu.cn., Wang LF; College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, P. R. China., Gui YY; College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, P. R. China., Zhang W; West China School of Public Health and West China Fourth Hospital, Sichuan University, Chengdu, 610041, P. R. China. dwzhang@scu.edu.cn., Yu DG; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. jhye@scu.edu.cn., Ye JH; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. jhye@scu.edu.cn.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Nov 05; Vol. 60 (89), pp. 13083-13086. Date of Electronic Publication: 2024 Nov 05.
DOI: 10.1039/d4cc03879g
Abstrakt: Dearomative functionalization of heteroarenes offers an attractive and sustainable approach for the rapid construction of complex 3D heterocyclic scaffolds from planar structures. Despite progress in this field, dearomative amination of heteroarenes via a radical anion intermediate remains a challenge. Here, we report a photoredox-catalyzed dearomative hydroamination of heteroarenes with hydrazodiformates under mild and transition-metal-free reaction conditions. Various benzofurans and benzothiophenes can efficiently participate in this transformation. A series of mechanistic experiments revealed that heteroaryl radical anions are the crucial intermediates, generated through photo-induced electron transfer between the excited phenolate photocatalyst and heteroarenes.
Databáze: MEDLINE
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