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
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
收藏
页码:9096 / 9106
页数:11
相关论文
共 39 条
  • [1] Palladium-Catalyzed Sequential C-H Activation/Amination of 2-Iodobiphenyls with Benzoisoxazoles for Synthesis of Carbazoles
    Zhao, Ya-Heng
    Chen, Jun-Hua
    Liu, Miao-Chang
    Zhou, Yun-Bing
    Wu, Hua-Yue
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (17) : 2939 - 2943
  • [2] Synthesis of Carbazoles from 2-Iodobiphenyls by Palladium-Catalyzed C-H Activation and Amination with Diaziridinone
    Shao, Changdong
    Zhou, Bo
    Wu, Zhuo
    Ji, Xiaoming
    Zhang, Yanghui
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (05) : 887 - 892
  • [3] Palladium-catalyzed coupling reaction of 2-iodobiphenyls with alkenyl bromides for the construction of 9-(diorganomethylidene)fluorenes
    Zhao, Ya-Heng
    Wang, Jian-Long
    Zhou, Yun-Bing
    Liu, Miao-Chang
    Wu, Hua-Yue
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (38) : 8250 - 8253
  • [4] Synthesis of Fluoren-9-ones via Pd-Catalyzed Annulation of 2-Iodobiphenyls with Vinylene Carbonate
    Li, Wenguang
    Yu, Yongqi
    Yang, Jie
    Fu, Kaifang
    Zhang, Xu
    Shi, Shukui
    Li, Ting
    CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (04)
  • [5] Synthesis of Tribenzo[b,d,f]azepines via Cascade π-Extended Decarboxylative Annulation Involving Cyclic Diaryliodonium Salts
    Hu, Tao
    Ye, Zenghui
    Zhu, Kai
    Xu, Kai
    Wu, Yanqi
    Zhang, Fengzhi
    ORGANIC LETTERS, 2020, 22 (02) : 505 - 509
  • [6] Synthesis of Dibenzo[b,f]azepines via Palladium-Catalyzed Cascade [4+3] Annulation of o-Alkenyl Bromoarenes and o-Bromoaniline Derivatives
    Zhan, Xin-Chen
    Lin, Guo-Qiang
    Fu, Jian-Guo
    Ji, Xiao-Ming
    Zhang, Shu-Sheng
    Feng, Chen-Guo
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (23) : 4127 - 4131
  • [7] Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzothiophenes via the Annulation of Aryl Sulfides with Alkynes
    Masuya, Yoshihiro
    Tobisu, Mamoru
    Chatani, Naoto
    ORGANIC LETTERS, 2016, 18 (17) : 4312 - 4315
  • [8] Palladium-catalyzed [4+3] annulation of 2-bromobiphenyls and epoxides for the assembly of dihydrodibenzo[b,d]oxepines
    Shen, Zipei
    Zhou, Lan
    Wu, Chenggui
    Zhou, Qianghui
    Cheng, Hong-Gang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (45) : 8869 - 8872
  • [9] Synthesis of N-Acylcarbazoles through Palladium-Catalyzed Aryne Annulation of 2-Haloacetanilides
    Lu, Chun
    Markina, Nataliya A.
    Larock, Richard C.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24) : 11153 - 11160
  • [10] Synthesis of Dihydroisobenzofurans via Palladium-Catalyzed Sequential Alkynylation/Annulation of 2-Bromobenzyl and 2-Chlorobenzyl Alcohols under Microwave Irradiation
    Buxaderas, Eduardo
    Alonso, Diego A.
    Najera, Carmen
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) : 3415 - 3421