Primary amides: Sustainable weakly coordinating groups in transition metal-catalyzed C-H bond functionalization reactions

被引:14
|
作者
Thakur, Rima [1 ]
Jaiswal, Yogesh [2 ]
Kumar, Amit [2 ]
机构
[1] Natl Inst Technol Patna, Dept Chem, Patna 800005, Bihar, India
[2] Indian Inst Technol Patna, Dept Chem, Bihta 801106, Bihar, India
关键词
Primary amide as a directing group; C-H activation; functionalization; Catalysis; N-heterocycles; Transition-metal salts (Pd; Rh; Ru); TRANSIENT DIRECTING GROUPS; PRIMARY BENZAMIDES; DIAZO-COMPOUNDS; SITE-SELECTIVITY; CARBOXYLIC-ACIDS; DIRECT ARYLATION; ARYL HALIDES; ACTIVATION; CYCLIZATION; ACCESS;
D O I
10.1016/j.tet.2021.132313
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The directing groups assisted transition-metal catalyzed functionalization of unreactive C-H bond is considered as one of the valuable alternative synthetic tools to the conventional organic synthesis. The significant challenges in these fields are the requirements of two extra steps: introduction and removal of the directing group. Therefore, recently specific attention has been paid to utilize the useful functional motifs as desired directing groups for the site-selective activation of C-H bonds. Primary amides are considered as one of the fundamental functional groups that play an essential role in chemistry and biology. The presence of N and O atoms in amides makes them an ideal substrate for the directing group in transition-metal catalyzed C-H activation reactions. In this report, we give a brief overview of the recent development of primary amides as sustainable coordinating directing groups for the site-selective activation of ortho-C-H bonds of aromatic compounds followed by annulation reactions to make different molecular architectures. (c) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:26
相关论文
共 50 条
  • [21] Heterocycle Construction via Transition Metal-Catalyzed C-H Functionalization and C-Heteroatom Bond Formation
    Liu, Yajun
    Kim, Jihye
    Chae, Junghyun
    CURRENT ORGANIC CHEMISTRY, 2014, 18 (16) : 2049 - 2071
  • [22] Traceless Directing Groups in Sustainable Metal-Catalyzed C-H Activation
    Zarkadoulas, Athanasios
    Zgouleta, Ioanna
    Tzouras, Nikolaos V.
    Vougioukalakis, Georgios C.
    CATALYSTS, 2021, 11 (05)
  • [23] New developments in transition metal-catalyzed synthetic reactions via C-H bond activation
    Fujiwara, Y
    Jia, CG
    PURE AND APPLIED CHEMISTRY, 2001, 73 (02) : 319 - 324
  • [24] Vinylene Carbonate as Synthon in Transition Metal-Catalyzed C-H Bond Activation/Annulation Reactions
    Cui, Xiaofan
    Chauvin, Remi
    Pi, Chao
    Wu, Yangjie
    Cui, Xiuling
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (20) : 3400 - 3412
  • [25] Metal-catalyzed C-H activation/functionalization: The fundamentals
    Roudesly, Fares
    Oble, Julie
    Poli, Giovanni
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2017, 426 : 275 - 296
  • [26] Transient Ligand-Enabled Transition Metal-Catalyzed C-H Functionalization
    Niu, Ben
    Yang, Ke
    Lawrence, Brianna
    Ge, Haibo
    CHEMSUSCHEM, 2019, 12 (13) : 2955 - 2969
  • [27] Metal-catalyzed C-H functionalization involving isocyanides
    Song, Bingrui
    Xu, Bin
    CHEMICAL SOCIETY REVIEWS, 2017, 46 (04) : 1103 - 1123
  • [28] Transition Metal-Catalyzed C-H Activation/Functionalization of 8-Methylquinolines
    Doraghi, Fatemeh
    Ashtiani, Mohammad Mahdi Aghanour
    Ameli, Mahmoud
    Larijani, Bagher
    Mahdavi, Mohammad
    CHEMICAL RECORD, 2024, 24 (11):
  • [29] Transition metal-catalyzed ketone-directed or mediated C-H functionalization
    Huang, Zhongxing
    Lim, Hee Nam
    Mo, Fanyang
    Young, Michael C.
    Dong, Guangbin
    CHEMICAL SOCIETY REVIEWS, 2015, 44 (21) : 7764 - 7786
  • [30] Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity
    Giri, Ramesh
    Shi, Bing-Feng
    Engle, Keary M.
    Maugel, Nathan
    Yu, Jin-Quan
    CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) : 3242 - 3272