Nickel-Catalyzed Secondary Benzylic C-O Bond Borylation

被引:1
|
作者
Li, Pengfei [1 ]
Zhang, Chenyan [1 ]
Wang, Jiaqi [1 ]
Zhang, Lei [1 ]
机构
[1] Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Hangzhou 310024, Peoples R China
基金
中国国家自然科学基金;
关键词
ARYL ETHERS; CARBON-OXYGEN; 2-PYRIDYL ETHERS; CROSS-COUPLINGS; METHYL ETHERS; ELECTROPHILES; ACTIVATION; REACTIVITY; CLEAVAGE;
D O I
10.1021/acs.orglett.4c02920
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A remote steric hindrance ligand (m-Bu- t)(2)C6H3PCy2 (L1) was synthesized to promote Ni-catalyzed C-O bond activation. The reaction achieved high yields for secondary benzylic C(sp(3))-O borylation in non-pi-extended systems under mild conditions. Mechanistic studies indicate that the nickel complex containing 1 equiv of L1 serves as the active catalyst, while increased loading of L1 gives the inactive bisligated Ni species. Acetanilide is crucial for the cross-coupling reaction, which facilitates generation of the monoligated nickel species.
引用
收藏
页码:7932 / 7937
页数:6
相关论文
共 50 条
  • [31] Nickel-catalyzed α-benzylation of sulfones with esters via C-O activation
    Xiao, Jing
    Yang, Jia
    Chen, Tieqiao
    Han, Li-Biao
    RSC ADVANCES, 2016, 6 (48) : 42656 - 42659
  • [32] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Reductive C-F and C-O Bond Cleavage
    Lin, Zhiyang
    Lan, Yun
    Wang, Chuan
    ACS CATALYSIS, 2019, 9 (01) : 775 - 780
  • [33] Nickel-catalyzed cross-couplings of alkyl electrophiles via C-N and C-O bond activation
    Basch, Corey
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [34] Nickel-Catalyzed Decarbonylative Borylation of Amides: Evidence for Acyl C-N Bond Activation
    Hu, Jiefeng
    Zhao, Yue
    Liu, Jingjing
    Zhang, Yemin
    Shi, Zhuangzhi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) : 8718 - 8722
  • [35] Nickel-Catalyzed Cross-Coupling of Aryl Pivalates with Cyclobutanols Involving C-O and C-C Bond Cleavage
    Gan, Yi
    Zhang, Ninghui
    Huang, Shaoxu
    Liu, Yuanhong
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1686 - 1690
  • [36] Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C-O Bond Cleavage
    Qin, Gan-Qi
    Wang, Jiao
    Cao, Xu-Rong
    Chu, Xue-Qiang
    Zhou, Xiaocong
    Rao, Weidong
    Zhai, Li-Xin
    Miao, Chengping
    Shen, Zhi-Liang
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13735 - 13743
  • [37] Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C-O Bond Cleavage
    Tobisu, Mamoru
    Takahira, Tsuyoshi
    Chatani, Naoto
    ORGANIC LETTERS, 2015, 17 (17) : 4352 - 4355
  • [38] Nickel-Catalyzed Cross-Coupling Reactions of Unreactive Phenolic Electrophiles via C-O Bond Activation
    Tobisu, Mamoru
    Chatani, Naoto
    TOPICS IN CURRENT CHEMISTRY, 2016, 374 (04)
  • [39] Nickel-Catalyzed Alkylative Cross-Coupling of Anisoles with Grignard Reagents via C-O Bond Activation
    Tobisu, Mamoru
    Takahira, Tsuyoshi
    Morioka, Toshifumi
    Chatani, Naoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (21) : 6711 - 6714
  • [40] Nickel-Catalyzed C-H/C-O Coupling of Azoles with Phenol Derivatives
    Muto, Kei
    Yamaguchi, Junichiro
    Itami, Kenichiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) : 169 - 172