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

共 87 条

[1] Catalytic enantioselective Pudovik reaction of aldehydes and aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex [J].

Abell, Joshua P. ;

Yamamoto, Hisashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) :10521-+

[2] FeCl3-Catalyzed synthesis of pyrrolo[1,2-a]-quinoxaline derivatives from 1-(2-aminophenyl)-pyrroles through annulation and cleavage of cyclic ethers [J].

An, Zhenyu ;

Zhao, Lianbiao ;

Wu, Mingzhong ;

Ni, Jixiang ;

Qi, Zhenjie ;

Yu, Guiqin ;

Yan, Rulong .

CHEMICAL COMMUNICATIONS, 2017, 53 (84) :11572-11575

[3]

Arbusow B.A., 1964, PURE APPL CHEM, V9, P307, DOI [10.1351/pac196409020307, DOI 10.1351/PAC196409020307]

[4] Identification of the Molecular Basis of Inhibitor Selectivity between the Human and Streptococcal Type I Methionine Aminopeptidases [J].

Arya, Tarun ;

Reddi, Ravikumar ;

Kishor, Chandan ;

Ganji, Roopa Jones ;

Bhukya, Supriya ;

Gumpena, Rajesh ;

McGowan, Sheena ;

Drag, Marcin ;

Addlagatta, Anthony .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (05) :2350-2357

[5] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].

Basle, Olivier ;

Li, Chao-Jun .

CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126

[6] THE MICHAELIS-ARBUZOV REARRANGEMENT [J].

BHATTACHARYA, AK ;

THYAGARAJAN, G .

CHEMICAL REVIEWS, 1981, 81 (04) :415-430

[7] Visible light-mediated C-P bond formation reactions [J].

Cai, Bao-Gui ;

Xuan, Jun ;

Xiao, Wen-Jing .

SCIENCE BULLETIN, 2019, 64 (05) :337-350

[8] 8-Mercaptoquinoline as a Ligand for Enhancing the Photocatalytic Activity of Pt(II) Coordination Complexes: Reactions and Mechanistic Insights [J].

Casado-Sanchez, Antonio ;

Uygur, Mustafa ;

Gonzalez-Munoz, Daniel ;

Aguilar-Galindo, Fernando ;

Luis Nova-Fernandez, Jose ;

Arranz-Plaza, Judith ;

Diaz-Tendero, Sergio ;

Cabrera, Silvia ;

Mancheno, Olga Garcia ;

Aleman, Jose .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) :6437-6447

[9] Catalyst-free direct C(sp3)-H sulfenylation of xanthene derivatives using air as the oxidant [J].

Chen, Qian ;

Yu, Guodian ;

Wang, Xiaofeng ;

Ou, Yingcong ;

Huo, Yanping .

GREEN CHEMISTRY, 2019, 21 (04) :798-802

[10] DDQ-mediated direct C(sp3)-H phosphorylation of xanthene derivatives [J].

Chen, Qian ;

Wang, Xiaofeng ;

Yu, Guodian ;

Wen, Chunxiao ;

Huo, Yanping .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (18) :2652-2656

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