Excited-state cobaloxime catalysis enabled scalable oxidant-free dehydrogenative C-H phosphinoylation of undirected heterocycles

被引：8

作者：

Shao, Ailong ^{[1
]}

Chen, Jifang ^{[1
]}

Wang, Lingxiao ^{[1
]}

Yi, Mingchen ^{[1
]}

Yang, Han ^{[1
]}

Zhang, Yuqing ^{[1
]}

Fan, Suhua ^{[1
]}

Chen, Shuisheng ^{[1
]}

Wu, Hai ^{[1
]}

Shi, Renyi ^{[2
]}

机构：

[1] Fuyang Normal Univ, Sch Chem & Mat Engn, Engn Res Ctr Biomass Convers & Pollut Prevent Anh, Anhui Prov Key Lab Degradat & Monitoring Pollut E, Fuyang 236037, Anhui, Peoples R China

[2] Xi An Jiao Tong Univ, Sch Chem Engn & Technol, Xian 710049, Shanxi, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 16期

关键词：

H/P-H; 6-PHOSPHORYLATED PHENANTHRIDINES; OXIDATIVE PHOSPHONATION; PHOTOREDOX CATALYSIS; UNACTIVATED ALKENES; COUPLING REACTIONS; TERTIARY-AMINES; METAL-FREE; SILVER; PHOSPHONYLATION;

D O I：

10.1039/d2qo00662f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light-induced, synergistic excited-state cobaloxime catalysis system has been developed to perform the dehydrogenative C(sp(2))-H phosphinoylation of various undirected bioactive molecules accompanied by H-2 evolution. This protocol is conducted under oxidant-free conditions and is featured with high regioselectivity as well as a broad substrate scope (more than 60 examples; yields up to 90%). Notably, the successful achievement for the C(sp(3))-H phosphinoylation of tetrahydroisoquinolines and the late-stage phosphinoylation of several marketed drugs further proves the potential synthetic utility of this approach. Mechanistic studies indicate that this transformation may proceed through a radical pathway.

引用

页码：4379 / 4387

页数：9

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