Palladium-Catalyzed [4+2] Annulation of Aryl and Alkenyl Carboxamides with 1,3-Dienes via C-H Functionalization: Synthesis of 3,4-Dihydroisoquinolones and 5,6-Dihydropyridinones

被引：22

作者：

Sun, Manman

Li, Jinshan

Chen, Weida

Wu, Haijian

Yang, Jianguo

Wang, Zhiming ^{[1
]}

机构：

[1] Taizhou Univ, Adv Res Inst, 1139 Shifu Ave, Taizhou 318000, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2020年 / 52卷 / 08期

关键词：

palladium; 4+2] annulation; carboxamides; dienes; C-H functionalization; 3,4-dihydroisoquinolones; 5,6-dihydropyridinones; COUPLED US28 RECEPTOR; BOND ACTIVATION; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; CASCADE; ACCESS; 2,3-DIHYDROBENZOFURANS; DERIVATIVES; AMIDATION; OLEFINS;

D O I：

10.1055/s-0039-1690219

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed [4+2] annulation of aryl and alkenyl carboxamides with 1,3-dienes via C-H functionalization is developed using air as the terminal oxidant. The method demonstrates good functional group tolerance and high stereoselectivity, affording a series of 3,4-dihydroisoquinolones and 5,6-dihydropyridinones in yields of up to 99%.

引用

收藏

页码：1253 / 1265

页数：13

相关论文

共 71 条

[1] Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5+2] Annulation of o-Arylanilines with Dienes [J].

Bai, Lu ;

Wang, Yan ;

Ge, Yicong ;

Liu, Jingjing ;

Luan, Xinjun .

ORGANIC LETTERS, 2017, 19 (07) :1734-1737

[2] Highly substituted pyrrolidinones and pyridones by 4-CR/2-CR sequence [J].

Beck, B ;

Picard, A ;

Herdtweck, E ;

Dömling, A .

ORGANIC LETTERS, 2004, 6 (01) :39-42

[3] Organocatalytic asymmetric 1,6-additions of β-ketoesters and glycine imine [J].

Bernardi, Luca ;

Lopez-Cantarero, Jesus ;

Niess, Barbara ;

Jlrgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5772-5778

[4] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

[5] Modular access to vicinally functionalized allylic (thio) morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides [J].

Braunstein, Hannah ;

Langevin, Spencer ;

Khim, Monique ;

Adamson, Jonathan ;

Hovenkotter, Katie ;

Kotlarz, Lindsey ;

Mansker, Brandon ;

Beng, Timothy K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (37) :8864-8872

[6] Palladium-Catalyzed Cascade sp2 C-H Functionalization/Intramolecular Asymmetric Allylation: From Aryl Ureas and 1,3-Dienes to Chiral Indolines [J].

Chen, Shu-Sen ;

Wu, Min-Song ;

Han, Zhi-Yong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (23) :6641-6645

[7] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].

Chen, Zhengkai ;

Wang, Binjie ;

Zhang, Jitan ;

Yu, Wenlong ;

Liu, Zhanxiang ;

Zhang, Yuhong .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295

[8] Asymmetric Synthesis of Isoquinoline Alkaloids: 2004-2015 [J].

Chrzanowska, Maria ;

Grajewska, Agnieszka ;

Rozwadowska, Maria D. .

CHEMICAL REVIEWS, 2016, 116 (19) :12369-12465

[9] Asymmetric synthesis of (+)- and (-)-latifine [J].

Couture, A ;

Deniau, E ;

Grandclaudon, P ;

Lebrun, S .

TETRAHEDRON-ASYMMETRY, 2003, 14 (10) :1309-1316

[10] Rh(III)-catalyzed C-H activation/cycloaddition of benzamides and methylenecyclopropanes: divergence in ring formation [J].

Cui, Sunliang ;

Zhang, Yan ;

Wu, Qifan .

CHEMICAL SCIENCE, 2013, 4 (09) :3421-3426

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