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
  • [1] Palladium-Catalyzed Carbonylative Multicomponent Reactions
    Shen, Chaoren
    Wu, Xiao-Feng
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (13) : 2973 - 2987
  • [2] Palladium-Catalyzed Carbonylative Synthesis of Heterocycles
    Feng, Jian-Bo
    Wu, Xiao-Feng
    HETEROCYCLIC CHEMISTRY IN THE 21ST CENTURY: A TRIBUTE TO ALAN KATRITZKY, 2017, 121 : 207 - 246
  • [3] Palladium-Catalyzed Benzylic C(sp3)-H Carbonylative Arylation with Aryl Bromides
    Hu, Bowen
    Zhao, Haoqiang
    Wu, Yu
    Walsh, Patrick J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (23)
  • [4] Palladium-Catalyzed Intramolecular Carbene Insertion into C(sp3)-H Bonds
    Sole, Daniel
    Mariani, Francesco
    Bennasar, M. -Lluisa
    Fernandez, Israel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (22) : 6467 - 6470
  • [5] Palladium-Catalyzed Amidation of Unactivated C(sp3)-H Bonds: from Anilines to Indolines
    Neumann, Julia J.
    Rakshit, Souvik
    Droege, Thomas
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6892 - 6895
  • [6] Palladium-Catalyzed Direct Arylation of C(sp3)-H Bonds of α-Cyano Aliphatic Amides
    Reddy, M. Damoder
    Watkins, E. Blake
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (22) : 11447 - 11459
  • [7] Palladium-Catalyzed Carbonylative Cyclization of Amines via γ-C(sp3)-H Activation: Late-Stage Diversification of Amino Acids and Peptides
    Hernando, Elier
    Villalva, Julia
    Manu Martinez, Angel
    Alonso, Ines
    Rodriguez, Nuria
    Gomez Arrayas, Ramon
    Carretero, Juan C.
    ACS CATALYSIS, 2016, 6 (10): : 6868 - 6882
  • [8] Palladium-Catalyzed Picolinamide-Directed Acetoxylation of Unactivated γ-C(sp3)-H Bonds of Alkylamines
    Li, Qiong
    Zhang, Shu-Yu
    He, Gang
    Nack, William A.
    Chen, Gong
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1544 - 1548
  • [9] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives
    Ano, Yusuke
    Tobisu, Mamoru
    Chatani, Naoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) : 12984 - 12986
  • [10] Direct Palladium-Catalyzed Carbonylative Transformation of Allylic Alcohols and Related Derivatives
    Wu, Fu-Peng
    Peng, Jin-Bao
    Fu, Lu-Yang
    Qi, Xinxin
    Wu, Xiao-Feng
    ORGANIC LETTERS, 2017, 19 (19) : 5474 - 5477