Oxidative Cross‐Dehydrogenative‐Coupling Reaction of 3,4‐Dihydro‐1,4‐Benzoxazin‐2‐ones through Visible‐Light Photoredox Catalysis | Zendy

Zhang GuoYan | Zendy; Yu KaiXin | Zendy; Zhang Chen | Zendy; Guan Zhi | Zendy; He YanHong | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research