Visible-Light-Induced α-C(sp3)-H Phosphinylation of Unactivated Ethers under Photocatalyst- and Additive-Free Conditions

被引：11

作者：

Liu, Bo ^{[1
]}

Li, Jianji ^{[1
]}

Hu, Yifan ^{[1
]}

Chen, Qian ^{[1
]}

Liu, Yan ^{[1
]}

Ji, Shaomin ^{[1
]}

Maruoka, Keiji ^{[2
]}

Huo, Yanping ^{[1
]}

Zhang, Hao-Li ^{[1
,3
]}

机构：

[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo, Kyoto 6068501, Japan

[3] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem SKLAOC, Key Lab Special Funct Mat & Struct Design,MOE, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 16期

基金：

中国国家自然科学基金;

关键词：

DEHYDROGENATIVE-COUPLING REACTIONS; C-H; PHOTOREDOX CATALYSIS; MICHAELIS-ARBUZOV; ALPHA-AMINOPHOSPHONATES; TERTIARY-AMINES; C(SP(3))-H; FUNCTIONALIZATION; PHOSPHONATES; DERIVATIVES;

D O I：

10.1021/acs.joc.2c01502

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photocatalyst-and additive-free visible-light-induced alpha-C(sp(3))-H phosphinylation of unactivated ethers involving a C-O bond cleavage with molecular oxygen as the sole oxidant at room temperature has been achieved. This method provides a sustainable access to alpha-hydroxyphosphine oxides in up to 88% yield with good functional group compatibility under mild and neutral conditions (34 examples). Moreover, the subsequent two-step conversion of the resulting dihydroxy diarylphosphine oxides afforded alpha-phosphinylated cyclic ethers in good overall yields (10 examples).

引用

页码：11281 / 11291

页数：11

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