Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Bromides and Chlorosilanes

被引:24
|
作者
Xing, Mimi [1 ]
Cui, Huanhuan [1 ]
Zhang, Chun [1 ,2 ]
机构
[1] Tianjin Univ, Tianjin Key Lab Mol Optoelect Sci, Inst Mol Plus, Dept Chem,Sch Sci, Tianjin 300072, Peoples R China
[2] Zhejiang Inst Tianjin Univ, Ningbo 315201, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
SILYLATION; HALIDES; ARENES;
D O I
10.1021/acs.orglett.1c02887
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel nickel-catalyzed highly selective reductive cross-coupling of alkyl bromides and chlorosilanes to construct the C-Si bond has been developed. Under benign reaction conditions, a series of structurally interesting organosilanes can be accessed without Ni-catalyzed isomerization. The utility of this chemistry is illustrated by further transformations of the product. Moreover, the radical mechanism of the reaction is illustrated by control experiments.
引用
收藏
页码:7645 / 7649
页数:5
相关论文
共 50 条
  • [41] Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides
    Sha, Yunfei
    Liu, Jiandong
    Wang, Liang
    Liang, Demin
    Wu, Da
    Gong, Hegui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (22) : 4887 - 4890
  • [42] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent
    Su, Mincong
    Huang, Xia
    Lei, Chuanhu
    Jin, Jian
    ORGANIC LETTERS, 2022, 24 (01) : 354 - 358
  • [43] Nickel-Catalyzed Cross-Coupling of Aryl Diazonium Salts with Aryl Bromides
    Zhang, Guofu
    Fu, Yu
    Xiang, Jicong
    Guan, Chenfei
    Sang, Zhimin
    Ding, Chengrong
    ORGANIC LETTERS, 2024, 26 (31) : 6687 - 6691
  • [44] Nickel-catalyzed cross-coupling reaction of alkynyl bromides with Grignard reagents
    Li, Qing-Han
    Ding, Yong
    Yang, Xue-Jun
    CHINESE CHEMICAL LETTERS, 2014, 25 (09) : 1296 - 1300
  • [45] Nickel-Catalyzed Direct Cross-Coupling of Aryl Fluorosulfates with Aryl Bromides
    Na, Jin-He
    Liu, Xiang
    Jing, Jia-Wen
    Wang, Jing
    Chu, Xue-Qiang
    Ma, Mengtao
    Xu, Hao
    Zhou, Xiaocong
    Shen, Zhi-Liang
    ORGANIC LETTERS, 2023, 25 (13) : 2318 - 2322
  • [46] Nickel-catalyzed cross-coupling reaction of alkynyl bromides with Grignard reagents
    Qing-Han Li
    Yong Ding
    Xue-Jun Yang
    Chinese Chemical Letters, 2014, 25 (09) : 1296 - 1300
  • [47] Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl Halides
    Zhu, Dianhu
    Lv, Leiyang
    Qu, Zihang
    Li, Chao-Jun
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10): : 6312 - 6322
  • [48] Nickel-Catalyzed Alkenylative Cross-Coupling Reaction of Alkyl Sulfides
    Ishizuka, Kentaro
    Seike, Hirofumi
    Hatakeyama, Takuji
    Nakamura, Masaharu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13117 - 13119
  • [49] Nickel-Catalyzed Reductive Csp3-Ge Coupling of Alkyl Bromides with Chlorogermanes
    Guo, Peng
    Pang, Xiaobo
    Wang, Ke
    Su, Pei-Feng
    Pan, Qiu-Quan
    Han, Guan-Yu
    Shen, Qian
    Zhao, Zhen-Zhen
    Zhang, Wenhua
    Shu, Xing-Zhong
    ORGANIC LETTERS, 2022, 24 (09) : 1802 - 1806
  • [50] Nickel-Catalyzed Reductive Coupling of Aryl Halides with Secondary Alkyl Bromides and Allylic Acetate
    Wang, Shulin
    Qian, Qun
    Gong, Hegui
    ORGANIC LETTERS, 2012, 14 (13) : 3352 - 3355