Palladium-Catalyzed [2+2+1] Oxidative Annulation of 4-Hydroxycoumarins with Unactivated Internal Alkynes: Access to Spiro Cyclopentadiene-Chroman-2,4-dione Complexes

被引：26

作者：

Peng, Shiyong ^{[1
,2
]}

Gao, Tao ^{[1
]}

Sun, Shaofa ^{[1
]}

Peng, Yanhong ^{[1
]}

Wu, Minghu ^{[1
]}

Guo, Haibing ^{[1
]}

Wang, Jian ^{[1
,2
]}

机构：

[1] Hubei Univ Sci & Technol, Hubei Collaborat Innovat Ctr Nonpower Nucl Techno, Coll Chem & Biol Sci, Shijiazhuang 437100, Hubei Province, Peoples R China

[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 2-3期

关键词：

CH activation; palladium-catalyzed oxidative annulations; 2+2+1] reactions; spiro complexes; N BOND FORMATION; C-H; COUPLING/CYCLIZATION; CYCLOADDITION; ACIDS; FUNCTIONALIZATION; BENZAMIDES; AIR;

D O I：

10.1002/adsc.201300893

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Herein, we report our new results regarding a palladium-catalyzed [2+2+1] oxidative annulation of 4-hydroxycoumarins with unactivated internal alkynes, which affords a new class of compounds: the spiro cyclopentadiene-chroman-2,4-diones.

引用

页码：319 / 324

页数：6

共 48 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[2]

Brase S, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P99

[3] 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

[4] Synthesis of dihydropyridines and pyridines from Imines and alkynes via C-H activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3645-3651

[5] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Do, Hien-Quang ;

Shabashov, Dmitry .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086

[6]

de Meijere A., 2004, METAL CATALYZED CROS

[7] Oxone as an inexpensive, safe, and environmentally benign oxidant for C-H bond oxygenation [J].

Desai, LV ;

Malik, HA ;

Sanford, MS .

ORGANIC LETTERS, 2006, 8 (06) :1141-1144

[8] Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C-H Bond Cleavage Using Dioxygen as Oxidant [J].

Ding, Shengtao ;

Shi, Zhuangzhi ;

Jiao, Ning .

ORGANIC LETTERS, 2010, 12 (07) :1540-1543

[9] Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions [J].

Engle, Keary M. ;

Mei, Tian-Sheng ;

Wasa, Masayuki ;

Yu, Jin-Quan .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :788-802

[10] Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity [J].

Giri, Ramesh ;

Shi, Bing-Feng ;

Engle, Keary M. ;

Maugel, Nathan ;

Yu, Jin-Quan .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3242-3272

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