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Oxidative Cross‐Dehydrogenative‐Coupling Reaction of 3,4‐Dihydro‐1,4‐Benzoxazin‐2‐ones through Visible‐Light Photoredox Catalysis
Author(s) -
Zhang GuoYan,
Yu KaiXin,
Zhang Chen,
Guan Zhi,
He YanHong
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701683
Subject(s) - iminium , chemistry , photoredox catalysis , photochemistry , nucleophile , catalysis , visible spectrum , nucleophilic addition , coupling reaction , oxidative coupling of methane , combinatorial chemistry , photocatalysis , organic chemistry , physics , optoelectronics
The cross‐dehydrogenative‐coupling (CDC) reaction of benzoxazin‐2‐ones through visible‐light photoredox catalysis was developed. In the process of the reaction, an α‐amino radical intermediate is generated by using Ru(bpy) 3 Cl 2 as a photoredox catalyst under visible‐light irradiation at room temperature. This intermediate is then oxidized, using O 2 as terminal oxidant, to give an iminium ion intermediate. The iminium ion reacts directly with various aromatic nucleophiles to give the desired cross‐coupling products in yields of up to 80 %. This work provides a sustainable and environmentally friendly method for the synthesis of 3,4‐dihydro‐1,4‐benzoxazin‐2‐one derivatives.