Carbon-Carbon Formation via Ni-Catalyzed Suzuki-Miyaura Coupling through C-CN Bond Cleavage of Aryl Nitrile

被引:112
|
作者
Yu, Da-Gang
Yu, Miao
Guan, Bing-Tao
Li, Bi-Jie
Zheng, Yang
Wu, Zhen-Hua
Shi, Zhang-Jie [1 ]
机构
[1] Peking Univ, BNLMS, Beijing 100871, Peoples R China
关键词
ARYLBORONIC ACIDS; INTRAMOLECULAR ARYLCYANATION; UNSYMMETRICAL BIARYLS; GRIGNARD-REAGENTS; O ACTIVATION; NICKEL; CHLORIDES; COMPLEXES; ETHERS; FUNCTIONALIZATION;
D O I
10.1021/ol901217m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Suzuki-Miyaura coupling of aryl nitriles with aryl/alkenyl boronic esters is reported. With this method, the cyano group could be applied as a protecting group of arenes and finally as a leaving group to further construct polyaryl scaffolds.
引用
收藏
页码:3374 / 3377
页数:4
相关论文
共 50 条
  • [1] Late-Stage Carbon Isotope Exchange of Aryl Nitriles through Ni-Catalyzed C-CN Bond Activation
    Reilly, Sean W.
    Lam, Yu-hong
    Ren, Sumei
    Strotman, Neil A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (12) : 4817 - 4823
  • [2] Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Arylboronic Acids and -Iminonitriles through C-CN Bond Activation
    Liu, Kui
    Tao, Shou-Wei
    Qian, Chun
    Zhu, Yong-Ming
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (34) : 4769 - 4775
  • [3] Synthesis of Biaryls through Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides by Carbon-Nitrogen Bond Cleavage
    Shi, Shicheng
    Meng, Guangrong
    Szostak, Michal
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (24) : 6959 - 6963
  • [4] Suzuki-Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon-Carbon Bonds
    Xia, Ying
    Wang, Jianchun
    Dong, Guangbin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (16) : 5347 - 5351
  • [5] C(sp3)-C(sp2) bond formation via Ni-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium organotrifluoroborates
    Molander, Gary A.
    Argintaru, O. Andreea
    Aron, Ioana
    Dreher, Spencer D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [6] Ni-Catalyzed Reconstruction of Carbon Frameworks via C-C Bond Cleavage Reactions
    Kimura, Masanari
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2018, 76 (12) : 1324 - 1331
  • [7] Comparison of Arylboron-Based Nucleophiles in Ni-Catalyzed Suzuki-Miyaura Cross-Coupling with Aryl Mesylates and Sulfamates
    Zhang, Na
    Hoffman, David J.
    Gutsche, Nicholas
    Gupta, Jayesh
    Percec, Virgil
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14): : 5956 - 5964
  • [8] Intramolecular Transfer of Pd Catalyst on Carbon-Carbon Triple Bond and Nitrogen-Nitrogen Double Bond in Suzuki-Miyaura Coupling Reaction
    Kamigawara, Takeru
    Sugita, Hajime
    Mikami, Koichiro
    Ohta, Yoshihiro
    Yokozawa, Tsutomu
    CATALYSTS, 2017, 7 (07):
  • [9] Palladium-Catalyzed Decarbonylative Suzuki-Miyaura Coupling of Amides To Achieve Biaryls via C-N Bond Cleavage
    Luo, Zhongfeng
    Xiong, Li
    Liu, Tinting
    Zhang, Yuqi
    Lu, Siqi
    Chen, Yuwen
    Guo, Weijie
    Zhu, Yulin
    Zeng, Zhuo
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17): : 10559 - 10568
  • [10] Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates
    Ueno, Satoshi
    Chatani, Naoto
    Kakiuchi, Fumitoshi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (19) : 6098 - +