Rh(III)-Catalyzed Selective C8-H Acylmethylation of Quinoline N-Oxides

被引：71

作者：

You, Chang ^{[1
]}

Pi, Chao ^{[1
]}

Wu, Yangjie ^{[1
]}

Cui, Xiuling ^{[1
]}

机构：

[1] Zhengzhou Univ, Dept Chem, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, Zhengzhou 450052, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 21期

关键词：

C8-H bond activation; acylmethylation; quninoline N-oxide; rhodium-catalyzed; C-H ACTIVATION; RELAY CARBENOID FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; SULFOXONIUM YLIDES; C-8; POSITION; BONDS; ALKYLATION; METAL; SULFONYLATION; ALLYLATION;

D O I：

10.1002/adsc.201800659

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A highly efficient Rh-catalyzed regioselective C8-H acylmethylation of quinoline N-oxides with sulfoxonium ylides using N-oxide as the directing group under air atmosphere has been developed. This transformation has the generality of a broad scope of substrates, avoids external oxidants, and provides an efficient protocol to C8-H acylmethylated quinolines.

引用

页码：4068 / 4072

页数：5

共 52 条

[1] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds [J].

Barday, Manuel ;

Janot, Christopher ;

Halcovitch, Nathan R. ;

Muir, James ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13117-13121

[2] Cobalt(III) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer [J].

Barsu, Nagaraju ;

Sen, Malay ;

Premkumar, J. Richard ;

Sundararaju, Basker .

CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1338-1341

[3] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[4] Regioselective Metal-Free Cross-Coupling of Quinoline N-Oxides with Boronic Acids [J].

Bering, Luis ;

Antonchick, Andrey P. .

ORGANIC LETTERS, 2015, 17 (12) :3134-3137

[5] Pd-Catalyzed Ortho-C HAcylation/Cross Coupling of Aryl Ketone O-Methyl Oximes with Aldehydes Using tert-Butyl Hydroperoxide as Oxidant [J].

Chan, Chun-Wo ;

Zhou, Zhongyuan ;

Chan, Albert S. C. ;

Yu, Wing-Yiu .

ORGANIC LETTERS, 2010, 12 (17) :3926-3929

[6] C8-Selective Acylation of Quinoline N-Oxides with α-Oxocarboxylic Acids via Palladium-Catalyzed Regioselective C-H Bond Activation [J].

Chen, Xiaopei ;

Cui, Xiuling ;

Wu, Yangjie .

ORGANIC LETTERS, 2016, 18 (15) :3722-3725

[7] "One-Pot" Approach to 8-Acylated 2-Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline N-Oxides [J].

Chen, Xiaopei ;

Cui, Xiuling ;

Wu, Yangjie .

ORGANIC LETTERS, 2016, 18 (10) :2411-2414

[8] Direct 2-acetoxylation of quinoline N-oxides via copper catalyzed C-H bond activation [J].

Chen, Xuan ;

Zhu, Chongwei ;

Cui, Xiuling ;

Wu, Yangjie .

CHEMICAL COMMUNICATIONS, 2013, 49 (61) :6900-6902

[9] C-H Bond Activation Reactions of Ethers That Generate Iridium Carbenes [J].

Conejero, Salvador ;

Paneque, Margarita ;

Poveda, Manuel L. ;

Santos, Laura L. ;

Carmona, Ernesto .

ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (04) :572-580

[10]

David T. J., 1994, FEBS LETT, V352, P54

← 1 2 3 4 5 6 →