Oxidative C-H functionalization of N-carbamoyl 1,2-dihydroquinolines

被引：16

作者：

Liu, Ziqiang ^{[1
,2
]}

Chen, Lei ^{[3
]}

Li, Jing ^{[4
]}

Liu, Ke ^{[4
]}

Zhao, Jiaqi ^{[4
]}

Xu, Mengmeng ^{[4
]}

Feng, Lei ^{[4
]}

Wan, Ren-zhong ^{[3
]}

Li, Wei ^{[2
]}

Liu, Lei ^{[1
,4
]}

机构：

[1] Shandong Univ, Shenzhen Res Inst, Shenzhen 518057, Peoples R China

[2] Shandong Univ Tradit Chinese Med, Dept Pharmaceut Anal, Sch Pharm, Jinan 250355, Shandong, Peoples R China

[3] Shandong Agr Univ, Coll Anim Sci & Vet Med, Tai An 271018, Shandong, Peoples R China

[4] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Shandong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 36期

关键词：

REISSERT-TYPE REACTION; TERTIARY-AMINES; BONDS ADJACENT; COUPLING REACTIONS; MOLECULAR-OXYGEN; ACYLIMINIUM IONS; CROSS; METAL; CATALYSIS; QUINOLINE;

D O I：

10.1039/c7ob01793f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modular and efficient method for the synthesis of alpha-substituted 1,2-dihydroquinolines is described. Under mild metal-free conditions, readily available N-carbamoyl 1,2-dihydroquinolines undergo oxidative C-H alkynylation, alkenylation, and allylation with a range of potassium trifluoroborates using TEMPO oxoammonium salt as an oxidant.

引用

页码：7600 / 7606

页数：7

共 81 条

[1] Mechanism of the oxidation of alcohols by oxoammonium cations [J].

Bailey, William F. ;

Bobbitt, James M. ;

Wiberg, Kenneth B. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) :4504-4509

[2]

Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/c3sc52265b, 10.1039/C3SC52265B]

[3] A highly enantioselective Mannich reaction of aldehydes with cyclic N-acyliminium ions by synergistic catalysis [J].

Berti, Francesco ;

Malossi, Federico ;

Marchetti, Fabio ;

Pineschi, Mauro .

CHEMICAL COMMUNICATIONS, 2015, 51 (71) :13694-13697

[4] A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline [J].

Boess, Esther ;

Schmitz, Corinna ;

Klussmann, Martin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5317-5325

[5] Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent [J].

Boess, Esther ;

Sureshkumar, Devarajulu ;

Sud, Abhishek ;

Wirtz, Cornelia ;

Fares, Christophe ;

Klussmann, Martin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8106-8109

[6] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

[7]

d'Acunzo F, 2002, EUR J ORG CHEM, V2002, P4195

[8] Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones [J].

Fu, Niankai ;

Li, Longji ;

Yang, Qi ;

Luo, Sanzhong .

ORGANIC LETTERS, 2017, 19 (08) :2122-2125

[9] Practical C-H Functionalization of Quinones with Boronic Acids [J].

Fujiwara, Yuta ;

Domingo, Victoriano ;

Seiple, Ian B. ;

Gianatassio, Ryan ;

Del Bel, Matthew ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3292-3295

[10] Combining Visible Light Catalysis and Transition Metal Catalysis for the Alkylation of Secondary Amines [J].

Gao, Xue-Wang ;

Meng, Qing-Yuan ;

Xiang, Ming ;

Chen, Bin ;

Feng, Ke ;

Tung, Chen-Ho ;

Wu, Li-Zhu .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) :2158-2164

← 1 2 3 4 5 6 7 8 9 →