Strain-Promoted Oxidative Annulation of Arynes and Cyclooctynes with Benzamides: Palladium-Catalyzed C-H/N-H Activation for the Synthesis of N-Heterocycles

被引：92

作者：

Peng, Xianglong ^{[1
]}

Wang, Weiguo ^{[1
]}

Jiang, Chao ^{[1
]}

Sun, Di ^{[1
]}

Xu, Zhenghu ^{[1
]}

Tung, Chen-Ho ^{[1
]}

机构：

[1] Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, Educ Minist, Jinan 250100, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 20期

关键词：

FUSED POLYCYCLIC AROMATICS; HIGHLY EFFICIENT ROUTE; METAL RELAY CATALYSIS; MOLECULAR-OXYGEN; INDOLE SYNTHESIS; BORONIC ACIDS; ARYL HALIDES; DEHYDROGENATIVE ANNULATION; INTRAMOLECULAR AMINATION; ISOQUINOLONE SYNTHESIS;

D O I：

10.1021/ol5025426

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Strained alkynes include arynes and cyclooctynes reacted with N-methoxyamides through palladium-catalyzed C-H/N-H activation for the first time. A variety of important N-heterocycles such as phenanthridinones and isoquinolones were constructed in one step with high efficiency.

引用

收藏

页码：5354 / 5357

页数：4

相关论文

共 102 条

[51] Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls [J].

Liu, ZJ ;

Zhang, XX ;

Larock, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15716-15717

[52] Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates [J].

Liu, ZJ ;

Larock, RC .

ORGANIC LETTERS, 2004, 6 (21) :3739-3741

[53] Palladium-Catalyzed Annulation of Arynes by o-Halobenzamides: Synthesis of Phenanthridinones [J].

Lu, Chun ;

Dubrovskiy, Anton V. ;

Larock, Richard C. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) :8648-8656

[54] Organocatalytic Oxidative Annulation of Benzamide Derivatives with Alkynes [J].

Manna, Srimanta ;

Antonchick, Andrey P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (28) :7324-7327

[55] Ruthenium-Catalyzed Cascade C-H Functionalization of Phenylacetophenones [J].

Mehta, Vaibhav P. ;

Garcia-Lopez, Jose-Antonio ;

Greaney, Michael F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) :1529-1533

[56] Regioselective Synthesis of Indoles via Rhodium-Catalyzed C-H Activation Directed by an In-Situ Generated Redox-Neutral Group [J].

Muralirajan, Krishnamoorthy ;

Cheng, Chien-Hong .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1571-1576

[57] RuII-Catalyzed Vinylative Dearomatization of Naphthols via a C(sp2)-H Bond Activation Approach [J].

Nan, Jiang ;

Zuo, Zhijun ;

Luo, Lei ;

Bai, Lu ;

Zheng, Huayu ;

Yuan, Yini ;

Liu, Jingjing ;

Luan, Xinjun ;

Wang, Yaoyu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (46) :17306-17309

[58] Synthesis of isochromenones and oxepines via Pd-catalyzed cascade cyclization of alkynes and benzynes involving C-H activation [J].

Parthasarathy, Kanniyappan ;

Han, Han ;

Prakash, Chandran ;

Cheng, Chien-Hong .

CHEMICAL COMMUNICATIONS, 2012, 48 (52) :6580-6582

[59] Access to Sultams by Rhodium(III)-Catalyzed Directed C-H Activation [J].

Pham, Manh V. ;

Ye, Baihua ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) :10610-10614

[60] Palladium-catalyzed cyclization of benzamides with arynes: application to the synthesis of phenaglydon and N-methylcrinasiadine [J].

Pimparkar, Sandeep ;

Jeganmohan, Masilamani .

CHEMICAL COMMUNICATIONS, 2014, 50 (81) :12116-12119

← 1 2 3 4 5 6 7 8 9 10 →