Catalyst-free benzylic C(sp3)-H functionalization of methyl quinolines with tryptanthrins

被引：5

作者：

Zheng, Zhu ^{[1
]}

Wu, Quanquan ^{[2
]}

Liu, Chong-Xing ^{[2
]}

Yang, Zhannan ^{[1
]}

Liu, Hongxin ^{[2
]}

机构：

[1] Guizhou Normal Univ, Key Lab Informat Syst Mt Areas & Protect Ecol Env, Guiyang, Guizhou, Peoples R China

[2] Wenzhou Univ, Coll Chem & Mat Sci, Wenzhou 325035, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2018年 / 48卷 / 09期

关键词：

2-Methyl quinoline; benzylic C(sp(3))-H functionalization; catalyst free; purification by centrifugation; tryptanthrins; C-H BOND; N-SULFONYL ALDIMINES; SITE-SELECTIVE SP(2); NUCLEOPHILIC-ADDITION; 2-METHYL AZAARENES; ALDOL REACTION; DERIVATIVES; ARYLATION; 2-ALKYLAZAARENES; ALKYLATION;

D O I：

10.1080/00397911.2018.1435820

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient method of catalyst free for the sp(3) C-H bond activation of methyl aza-arene and nucleophilic addition to tryptanthrins in DMF was developed. Importantly, the more efficient and green isolation strategy of the purification of the products by centrifugation with 90% yields was applied.

引用

页码：1092 / 1098

页数：7

共 60 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2]

Atul K., 2015, GREEN CHEM, V17, P848

[3] Palladium-Catalyzed Benzylic Arylation of 2-Methyl Azaarenes [J].

Burton, Paul M. ;

Morris, James A. .

ORGANIC LETTERS, 2010, 12 (23) :5359-5361

[4] Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].

Campeau, Louis-Charles ;

Schipper, Derek J. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+

[5] Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes [J].

Chatani, N ;

Asaumi, T ;

Yorimitsu, S ;

Ikeda, T ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10935-10941

[6] Catalytic functionalization of tertiary alcohols to fully substituted carbon centres [J].

Chen, Long ;

Yin, Xiao-Ping ;

Wang, Cui-Hong ;

Zhou, Jian .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (32) :6033-6048

[7] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways [J].

Chen, Xiao ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12634-12635

[8] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[9] TOTAL SYNTHESIS OF (+/-)-MITOMYCINS VIA ISOMITOMYCIN-A [J].

FUKUYAMA, T ;

YANG, LH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7881-7882

[10] Total Synthesis of a Pyrroloindoloquinazoline Alkaloid [J].

Gahtory, Digvijay ;

Chouhan, Mangilal ;

Sharma, Ratnesh ;

Nair, Vipin A. .

ORGANIC LETTERS, 2013, 15 (15) :3942-3945

← 1 2 3 4 5 6 →