Chan-Lam Reaction and Lewis Acid Promoted 1,3-Rearrangement of N-O Bonds to Prepare N-(2-Hydroxyaryl)pyridin-2-ones

被引：14

作者：

Bi, Hong-Yan ^{[1
,2
]}

Wu, Qing-Yan ^{[2
]}

Zhou, Xiao-Mei ^{[1
]}

Xu, Hui-Juan ^{[1
]}

Liang, Cui ^{[2
]}

Mo, Dong-Liang ^{[2
]}

Ma, Xiao-Pan ^{[1
]}

机构：

[1] Guilin Med Univ, Coll Pharm, Guilin 541199, Peoples R China

[2] Guangxi Normal Univ, Collaborat Innovat Ctr Guangxi Ethn Med, Sch Chem & Pharmaceut Sci, State Key Lab Chem & Mol Engn Med Resources, Guilin 541004, Peoples R China

来源：

ORGANIC LETTERS | 2022年

关键词：

ARYLATION; INHIBITORS; DESIGN;

D O I：

10.1021/acs.orglett.2c01827

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the difunctionalization of arylboronic acids to prepare various N-(2-hydroxyaryl)pyridin-2-ones in good yields using N-hydroxypyridin-2-ones as the oxygen and nitrogen sources through a copper(II)-catalyzed Chan-Lam reaction and subsequent BF3 promoted selective 1,3-rearrangement of N-O bond in a one-pot procedure. Mechanistic studies reveal that the 1,3-rearrangement selectivity is controlled by the formation of the key aryloxypyridinium salt. The obtained products are easily converted to various useful pyridin-2-one scaffolds.

引用

页码：4675 / 4679

页数：5

共 38 条

[1] Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines [J].

Altman, Ryan A. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2007, 9 (04) :643-646

[2]

[Anonymous], CCDC 2151659 4A CONT

[3] Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles [J].

Bi, Hong-Yan ;

Li, Cheng-Jing ;

Wei, Cui ;

Liang, Cui ;

Mo, Dong-Liang .

GREEN CHEMISTRY, 2020, 22 (17) :5815-5821

[4] Synthesis of a Leucomitosane via a Diastereoselective Radical Cascade [J].

Brucelle, Francois ;

Renaud, Philippe .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12) :6245-6252

[5] Oxoarylation of ynamides with N-aryl hydroxamic acids [J].

Chen, Changwei ;

Zhang, Hongyu ;

Xu, Gang ;

Cui, Sunliang .

CHINESE CHEMICAL LETTERS, 2021, 32 (08) :2551-2554

[6] A Review on the Latest Progress of Chan-Lam Coupling Reaction [J].

Chen, Jin-Quan ;

Li, Jing-Hang ;

Dong, Zhi-Bing .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (16) :3311-3331

[7] Cu-mediated selective O-arylation on C-6 substituted pyridin-2-ones [J].

Chen, Taijie ;

Huang, Qingqing ;

Luo, Yu ;

Hu, Youhong ;

Lu, Wei .

TETRAHEDRON LETTERS, 2013, 54 (11) :1401-1404

[8] The ortho hydroxy-amino group: Another choice for synthesizing novel antioxidants [J].

Chen, Weijun ;

Guo, Ping ;

Song, Jirong ;

Cao, Wei ;

Bian, Jiang .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (13) :3582-3585

[9] Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones [J].

Chen, Zhilong ;

Wang, Qiu .

ORGANIC LETTERS, 2015, 17 (24) :6130-6133

[10] Tellurium(II)/Tellurium(III)-Catalyzed Cross-Dehydrogenative C-N Bond Formation [J].

Cremer, Christopher ;

Goswami, Monalisa ;

Rank, Christian K. ;

de Bruin, Bas ;

Patureau, Frederic W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (12) :6451-6456

← 1 2 3 4 →