α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds

被引:5
|
作者
Wang, Mei [1 ]
Wang, Wei [1 ]
Li, Dashan [1 ]
Wang, Wen-Jing [1 ]
Zhan, Rui [2 ]
Shao, Li-Dong [1 ]
机构
[1] Yunnan Univ Chinese Med, Sch Chinese Mat Med, Yunnan Key Lab Southern Med Utilizat, Kunming 650050, Yunnan, Peoples R China
[2] Yunnan Normal Univ, Sch Chem & Chem Engn, Kunming 650050, Yunnan, Peoples R China
关键词
C-H functionalization; alpha-C(sp3)-H arylation; Cyclic carbonyl compounds; CATALYZED ALPHA-ARYLATION; C-H FUNCTIONALIZATION; ASYMMETRIC ARYLATION; VINYLOGOUS ESTERS; CONCISE SYNTHESIS; FACILE SYNTHESIS; SIMPLE OLEFINS; ARYL HALIDES; PALLADIUM; KETONES;
D O I
10.1007/s13659-021-00312-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
alpha-C(sp(3))-H arylation is an important type of C-H functionalization. Various biologically significant natural products, chemical intermediates, and drugs have been effectively prepared via C-H functionalization. Cyclic carbonyl compounds comprise of cyclic ketones, enones, lactones, and lactams. The alpha-C(sp(3))-H arylation of these compounds have been exhibited high efficiency in forming C(sp(3))-C(sp(2)) bonds, played a crucial role in organic synthesis, and attracted majority of interests from organic and medicinal communities. This review focused on the most significant advances including methods, mechanism, and applications in total synthesis of natural products in the field of alpha-C(sp(3))-H arylations of cyclic carbonyl compounds in recent years.
引用
下载
收藏
页码:379 / 404
页数:26
相关论文
共 50 条
  • [41] Mild C(sp3)-H Alkylation of 8-Methylquinolines with α,β-Unsaturated Carbonyl Compounds by Rhodium(III) Catalysis
    Han, Shengnan
    Ma, Wenbo
    Zhang, Zhao
    Liu, Lei
    Tang, Mengyao
    Li, Jie
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (08) : 1014 - 1018
  • [42] Auto-oxidation promoted sp3 C-H arylation of glycine derivatives
    Wei, Yuanyuan
    Wang, Jie
    Wang, Yajun
    Yao, Xiaoqiang
    Yang, Caixia
    Huo, Congde
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (27) : 4985 - 4989
  • [43] Nano palladium catalyzed C(sp3)-H bonds arylation by a transient directing strategy
    Chen, Jianxia
    Bai, Chaolumen
    Ma, Hongpeng
    Liu, Dan
    Bao, Yong-Sheng
    CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 465 - 469
  • [44] 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)
  • [45] Arylation of Aniline C(sp3)-H Bonds with Phenols via an In Situ Activation Strategy
    Gui, Yong-Yuan
    Wang, Zi-Xiao
    Zhou, Wen-Jun
    Liao, Li-Li
    Song, Lei
    Yin, Zhu-Bao
    Li, Jing
    Yu, Da-Gang
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (03) : 537 - 541
  • [46] Highly regloselective arylation of Sp3 C-H bonds catalyzed by palladium acetate
    Zaitsev, VG
    Shabashov, D
    Daugulis, O
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) : 13154 - 13155
  • [47] Asymmetric, Remote C(sp3)-H Arylation via Sulfinyl-Smiles Rearrangement
    Hu, Yawen
    Hervieu, Cedric
    Merino, Estibaliz
    Nevado, Cristina
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (17)
  • [48] Methylene C(sp3)-H Arylation of Aliphatic Ketones Using a Transient Directing Group
    Hong, Kai
    Park, Hojoon
    Yu, Jin-Quan
    ACS CATALYSIS, 2017, 7 (10): : 6938 - 6941
  • [49] Nickel-Catalyzed Direct C (sp3)-H Arylation of Aliphatic Amides with Thiophenes
    Wang, Xie
    Zhu, Longzhi
    Chen, Sihai
    Xu, Xinhua
    Au, Chak-Tong
    Qu, Renhua
    ORGANIC LETTERS, 2015, 17 (21) : 5228 - 5231
  • [50] Highly Regioselective Carbonylation of Unactivated C(sp3)-H Bonds by Ruthenium Carbonyl
    Hasegawa, Nao
    Charra, Valentine
    Inoue, Satoshi
    Fukumoto, Yoshiya
    Chatani, Naoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) : 8070 - 8073