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
  • [41] Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)-H Bonds
    He, Gang
    Zhang, Shu-Yu
    Nack, William A.
    Li, Qiong
    Chen, Gong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (42) : 11124 - 11128
  • [42] Recent Advances in Palladium-Catalyzed C(sp3)-H Activation for the Formation of Carbon-Carbon and Carbon-Heteroatom Bonds
    Dastbaravardeh, Navid
    Christakakou, Maria
    Haider, Maximilian
    Schnuerch, Michael
    SYNTHESIS-STUTTGART, 2014, 46 (11): : 1421 - 1439
  • [43] Palladium-Catalyzed Carbonylative Synthesis of Benzogerminones
    Chen, Bo
    Wu, Xiao-Feng
    SYNLETT, 2019, 30 (13) : 1592 - 1596
  • [44] Palladium-Catalyzed Carbonylation of Coumarin C( sp2)-H Bonds: A New Entry to Arylcoumarin Ketones
    Mirzaei, Siyavash
    Rajai-Daryasarei, Saideh
    Soheilizad, Mehdi
    Kabiri, Roya
    Ansari, Samira
    Shabanian, Meisam
    Pashazadeh, Rahim
    SYNTHESIS-STUTTGART, 2019, 51 (07): : 1680 - 1688
  • [45] Palladium-Catalyzed Carbonylative α-Arylation to β-Ketonitriles
    Schranck, Johannes
    Burhardt, Mia
    Bornschein, Christoph
    Neumann, Helfried
    Skrydstrup, Troels
    Beller, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (31) : 9534 - 9538
  • [46] Palladium Catalyzed Arylation of C(sp3)-H Bonds of Carbonyl β-position in Water
    Luo Feihua
    Long Yang
    Li Zhengkai
    Zhou Xiangge
    ACTA CHIMICA SINICA, 2016, 74 (10) : 805 - 810
  • [47] A Convenient and Efficient Palladium-Catalyzed Carbonylative Sonogashira Transformation with Formic Acid as the CO Source
    Peng, Jin-Bao
    Wu, Fu-Peng
    Li, Chong-Liang
    Qi, Xinxin
    Wu, Xiao-Feng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (11) : 1434 - 1437
  • [48] Palladium-Catalyzed Cross-Dehydrogenative Functionalization of C(sp2)-H Bonds
    Wu, Yinuo
    Wang, Jun
    Mao, Fei
    Kwong, Fuk Yee
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (01) : 26 - 47
  • [49] Palladium(II)-Catalyzed Directed Trifluoromethylthiolation of Unactivated C(sp3)-H Bonds
    Xiong, Heng-Ying
    Besset, Tatiana
    Cahard, Dominique
    Pannecoucke, Xavier
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) : 4204 - 4212
  • [50] Palladium-Catalyzed Carbonylative Difunctionalization of C=N Bond of Azaarenes or Imines to Quinazolinones
    Zhou, Xibing
    Ding, Yongzheng
    Huang, Hanmin
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (11) : 1678 - 1682