Indium-catalyzed C(sp3)-H functionalization of 2-methylazaarenes through direct benzylic addition to trifluoromethyl ketones

被引：21

作者：

Jamal, Zaini ^{[1
]}

Teo, Yong-Chua ^{[1
]}

机构：

[1] Nanyang Technol Univ, Natl Inst Educ, Nat Sci & Sci Educ, Singapore 637616, Singapore

来源：

RSC ADVANCES | 2015年 / 5卷 / 34期

关键词：

H BOND FUNCTIONALIZATION; ASYMMETRIC ALLYLIC ALKYLATIONS; N-SULFONYL ALDIMINES; ORGANIC-SYNTHESIS; TRANSITION-METAL; C-C; NUCLEOPHILIC-ADDITION; 2-ALKYL AZAARENES; METHYL AZAARENES; AQUEOUS-MEDIA;

D O I：

10.1039/c4ra17182a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The application of trivalent indium for the Lewis acid-catalyzed C(sp(3))-H functionalization of 2-methylazaarenes is reported. InCl3 was discovered to catalyze the direct addition of the benzylic C-H bond in the azaarenes to trifluoromethyl ketones. An ample number of substrates were cogently demonstrated to give the products as tri-fluoromethylated alcohols whereby in some cases, up to quantitative yield (99%) could be obtained.

引用

页码：26949 / 26953

页数：5

共 67 条

[41] Low-Oxidation State Indium-Catalyzed C-C Bond Formation [J].

Schneider, Uwe ;

Kobayashi, Shu .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (08) :1331-1344

[42] Organoindium Reagents: The Preparation and Application in Organic Synthesis [J].

Shen, Zhi-Liang ;

Wang, Shun-Yi ;

Chok, Yew-Keong ;

Xu, Yun-He ;

Loh, Teck-Peng .

CHEMICAL REVIEWS, 2013, 113 (01) :271-401

[43] Modern synthetic methods for fluorine-substituted target molecules [J].

Shimizu, M ;

Hiyama, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) :214-231

[44] A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation [J].

Tanaka, Yusuke ;

Ishihara, Takashi ;

Konno, Tsutomu .

JOURNAL OF FLUORINE CHEMISTRY, 2012, 137 :99-104

[45] Construction of Nitrogen-Containing Heterocycles by C-H Bond Functionalization [J].

Thansandote, Praew ;

Lautens, Mark .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (24) :5874-5883

[46] A catalytic approach for the functionalization of C(sp3)-H bonds [J].

Tobisu, M ;

Chatani, N .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) :1683-1684

[47] Strategy for Employing Unstabilized Nucleophiles in Palladium-Catalyzed Asymmetric Allylic Alkylations [J].

Trost, Barry M. ;

Thaisrivongs, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) :14092-+

[48] Palladium-Catalyzed Asymmetric Allylic Alkylations of Polynitrogen-Containing Aromatic Heterocycles [J].

Trost, Barry M. ;

Thaisrivongs, David A. ;

Hartwig, Jan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) :12439-12441

[49] Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Benzylic Allylation of 2-Substituted Pyridines [J].

Trost, Barry M. ;

Thaisrivongs, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12056-+

[50] Reductive Alkylation of Indoles with Alkynes and Hydrosilanes under Indium Catalysis [J].

Tsuchimoto, Teruhisa ;

Kanbara, Mitsutaka .

ORGANIC LETTERS, 2011, 13 (05) :912-915

← 1 2 3 4 5 6 7 →