Palladium-Catalyzed Carbonylative Transformation of C(sp3)-X Bonds

被引：161
|
作者：
Wu, Lipeng [1 ]
Fang, Xianjie [1 ]
Liu, Qiang [1 ]
Jackstell, Ralf [1 ]
Beller, Matthias [1 ]
Wu, Xiao-Feng [1 ]
机构：
[1] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
来源：
ACS CATALYSIS | 2014年 / 4卷 / 09期
关键词：
palladium catalyst; carbonylation; C(sp(3))-X bonds; cross-coupling; carbon monoxide; C-H BONDS; TRISULFONATED TRIPHENYLPHOSPHINE COMPLEXES; NOBLE METAL COMPOUNDS; ORGANIC ALLYL MOIETIES; BETA-KETO-ESTERS; CARBON-MONOXIDE; BETA; GAMMA-UNSATURATED ESTERS; ARYL HALIDES; OXIDATIVE CARBONYLATION; COUPLING REACTIONS;
D O I：
10.1021/cs500922x
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
During the last 50 years, the palladium-catalyzed carbonylation reactions underwent continuous development. Apart from carbonylation of aromatic (pseudo)-halide and alkene (C-sp(2)) compounds, the use of C(sp(3))-X compounds such as allyl compounds, benzyl compounds, and aliphatic alkanes have become the most useful tool for the synthesis of beta,gamma-unsaturated carbonyl compounds, aliphatic carboxylic acid, and their derivatives. The recently budding development in the area of palladium-catalyzed C(sp(3))-X (especially X = H) activation makes us feel it necessary to file a summary on the past, current contributions, and a prospective outlook on the palladium-catalyzed carbonylative transformation of C(sp(3)) X bonds, which is the focus of this review.
引用
收藏
页码：2977 / 2989
页数：13
相关论文
共 50 条
  • [31] Palladium-catalyzed intermolecular amination of unactivated C(sp3)-H bonds via a cleavable directing group
    Jin, Lianwen
    Zeng, Xiaoli
    Li, Siyang
    Hong, Xuechuan
    Qiu, Guofu
    Liu, Peng
    CHEMICAL COMMUNICATIONS, 2017, 53 (28) : 3986 - 3989
  • [32] Palladium-Catalyzed Triarylation of sp3 C-H Bonds in Heteroarylmethanes: Synthesis of Triaryl(heteroaryl)methanes
    Zhang, Shuguang
    Hu, Bowen
    Zheng, Zhipeng
    Walsh, Patrick J.
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (07) : 1493 - 1498
  • [33] Synthesis of Amides and Esters by Palladium(0)-Catalyzed Carbonylative C(sp3)-H Activation
    Carny, Tomas
    Rocaboy, Ronan
    Clemenceau, Antonin
    Baudoin, Olivier
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (43) : 18980 - 18984
  • [34] Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)-H bonds at room temperature
    Yang, Xinglin
    Sun, Yonghui
    Sun, Tian-yu
    Rao, Yu
    CHEMICAL COMMUNICATIONS, 2016, 52 (38) : 6423 - 6426
  • [35] Formation of C(sp3)-C(sp3) Bonds by Palladium Catalyzed Cross-Coupling of α-Diazoketones and Allylboronic Acids
    Belhomme, Marie-Charlotte
    Wang, Dong
    Szabo, Kalman J.
    ORGANIC LETTERS, 2016, 18 (10) : 2503 - 2506
  • [36] Palladium-Catalyzed C(sp3)-H Bond Functionalization of Aliphatic Amines
    He, Chuan
    Whitehurst, William G.
    Gaunt, Matthew J.
    CHEM, 2019, 5 (05): : 1031 - 1058
  • [37] Palladium-catalyzed methylene C(sp3)-H arylation of the adamantyl scaffold
    Lao, Ye-Xing
    Wu, Jia-Qiang
    Chen, Yunyun
    Zhang, Shang-Shi
    Li, Qingjiang
    Wang, Honggen
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10): : 1374 - 1378
  • [38] Palladium-Catalyzed Oxidative Carbonylation of Benzylic C-H Bonds via Nondirected C(sp3)-H Activation
    Xie, Pan
    Xie, Yinjun
    Qian, Bo
    Zhou, Han
    Xia, Chungu
    Huang, Hanmin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) : 9902 - 9905
  • [39] Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)-H and C(sp3)-H Bonds at δ- and ε-Positions
    Wang, Chao
    Chen, Changpeng
    Zhang, Jingyu
    Han, Jian
    Wang, Qian
    Guo, Kun
    Liu, Pei
    Guan, Mingyu
    Yao, Yingming
    Zhao, Yingsheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) : 9884 - 9888
  • [40] Palladium-Catalyzed Carbonylative Dimerization of Styrenes to 1,5-Diarylpent-1-en-3-ones
    Wu, Xiao-Feng
    Neumann, Helfried
    Beller, Matthias
    CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (06) : 1199 - 1202
12345