Synthesis of Tribenzo[b,d,f]azepines via Palladium-Catalyzed Annulation Reaction of 2-Iodobiphenyls with 2-Halogenoanilines

被引：12

作者：

Fang, Mao-Ying ^{[1
]}

Chen, Li-Ping ^{[1
]}

Huang, Lin ^{[1
]}

Fang, Dong-Mei ^{[2
]}

Chen, Xiao-Zhen ^{[2
]}

Wang, Bi-Qin ^{[1
]}

Feng, Chun ^{[1
]}

Xiang, Shi-Kai ^{[1
]}

机构：

[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 13期

基金：

中国国家自然科学基金;

关键词：

C-H ACTIVATION; 2-LODOBIPHENYLS; PALLADACYCLES; CARBAZOLES; FLUORENES;

D O I：

10.1021/acs.joc.1c01082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed annulation reaction of 2-iodobiphenyls with 2-halogenoanilines has been developed. A variety of 2-iodobiphenyls and 2-halogenoanilines can undergo this transformation. Diversified tribenzo[b,d,f]azepine derivatives can be synthesized in moderate to excellent yields according to this method.

引用

页码：9096 / 9106

页数：11

共 39 条

[31] Rh(III)-Catalyzed Reaction of 2-Aryl-3-acyl-1H-indoles with α-Diazo Carbonyl Compounds: Synthesis of 5-Carbonyl Substituted Benzo[a]carbazoles via [5+1] Annulation [J].

Li, Bin ;

Shen, Nana ;

Wang, Kelin ;

Fan, Xuesen ;

Zhang, Xinying .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (03)

[32] Palladium-catalyzed direct ortho C-X bond construction via C-H activation of azobenzenes: Synthesis of (E)-1,2-b(2,6-dibromo(chloro)-phenyl)diazene [J].

Liu, Qingqing ;

Luo, Xinxin ;

Wei, Shujie ;

Wang, Youzhao ;

Zhu, Jiaxin ;

Liu, Yi ;

Quan, Fenglei ;

Zhang, Meng ;

Xia, Chengcai .

TETRAHEDRON LETTERS, 2019, 60 (26) :1715-1719

[33] Palladium@Cerium(IV) Oxide-Catalyzed Oxidative Synthesis of N-(2-Pyridyl)indoles via C-H Activation Reaction [J].

Chen, Jianbin ;

He, Lin ;

Natte, Kishore ;

Neumann, Helfried ;

Beller, Matthias ;

Wu, Xiao-Feng .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) :2955-2959

[34] Synthesis of 6H-isoindolo[2,1-a]indol-6-ones through a sequential copper-catalyzed C-N coupling and palladium-catalyzed C-H activation reaction [J].

He, Hua-Feng ;

Dong, Sheng ;

Chen, Yi ;

Yang, Yang ;

Le, Yueqin ;

Bao, Weiliang .

TETRAHEDRON, 2012, 68 (14) :3112-3116

[35] Synthesis of [60]Fullerene-Fused Tetralones via Palladium-Catalyzed Ketone-Directed sp2 C-H Activation and sp3 C-H Functionalization [J].

Zhou, Dian-Bing ;

Wang, Guan-Wu .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (10) :1548-1554

[36] Rhodium-Catalyzed Spiro Indenyl Benzoxazine Synthesis via C-H Activation/Annulation of 3-Aryl-2H-Benzo[b][1,4]oxazines and Alkynes [J].

Tan, Heng ;

Laishram, Ronibala Devi ;

Zhang, Xuexin ;

Shi, Guangrui ;

Li, Kangkui ;

Chen, Jingchao .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (29) :4542-4546

[37] Palladium-Catalyzed Oxidative Cyclocarbonylation of Isoquinolones with CO via C-H/N-H Bond Cleavage: Easy Access to Isoindolo[2,1-b]isoquinoline-5,7-dione Derivatives [J].

Guo, Shenghai ;

Wang, Fang ;

Sun, Lincong ;

Zhang, Xinying ;

Fan, Xuesen .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) :2537-2545

[38] Palladium-Catalyzed and Hybrid Acids-Assisted Synthesis of [60]Fulleroazepines in One Pot under Mild Conditions: Annulation of N-Sulfonyl-2-aminobiaryls with [60]Fullerene through Sequential C-H Bond Activation, C-C and C-N Bond Formation [J].

Rajeshkumar, Venkatachalam ;

Chan, Fu-Wei ;

Chuang, Shih-Ching .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (13) :2473-2483

[39] Rhodaelectro-Catalyzed Synthesis of Pyrano[3,4-b]indol-1(9H)-ones via the Double Dehydrogenative Heck Reaction between Indole-2-carboxylic Acids and Alkenes [J].

Xiao, Fengyi ;

Xu, Xinlu ;

Zhang, Jiaqi ;

Chen, Ximan ;

Ruan, Xin ;

Wei, Qi ;

Zhang, Xiaofeng ;

Huang, Qiufeng .

JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (23) :17550-17561

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