Recent advances in nickel catalyzed Suzuki-Miyaura cross coupling reaction via C-O& C-N bond activation

被引:16
作者
Baviskar, Bhushan A. [1 ]
Ajmire, Prashant V. [2 ]
Chumbhale, Deshraj S. [3 ]
Khan, Mohammad Sadat [4 ]
Kuchake, Vitthal G. [4 ]
Singupuram, Madhavi [5 ]
Laddha, Purushottam R. [6 ]
机构
[1] Govt Coll Pharm, Dept Pharmaceut Chem, Amravati 444604, Maharashtra, India
[2] Dr Rajendra Gode Inst Pharm, Dept Pharm, Amravati 444604, Maharashtra, India
[3] Amrutvahini Coll Pharm, Dept Pharm, Ahmednagar 422608, Maharashtra, India
[4] OJAS Coll Pharm, Dept Pharmaceut Chem, Jalna 431203, Maharashtra, India
[5] Andhra Univ, Dept Organ Chem, Vishakhapatnam 530003, Andhra Pradesh, India
[6] Laddhad Coll Pharm, Dept Pharmaceut Chem, Buldhana 443001, Maharashtra, India
来源
SUSTAINABLE CHEMISTRY AND PHARMACY | 2023年 / 32卷
关键词
Suzuki-miyaura coupling; Transition metal catalysis; Earth abundant metals; C-O & C-N bond activation; DECARBOXYLATIVE ALKYLATION; DECARBONYLATIVE BORYLATION; PALLADIUM; AMIDES; ARYL; ESTERS; CLEAVAGE; LIGAND; PROTODEBORONATION; INTERCONVERSION;
D O I
10.1016/j.scp.2022.100953
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Research on transition metal catalysis is advancing day by day. Unlike the conventional precious metal based catalysis, the researchers are now focussing on exploring the applicability of earthabundant first row transition elements as catalysts for C-C coupling reactions. Among them, the Suzuki-Miyaura coupling reaction greatly impacts the industrial catalytic processes. Nickel catalyzed Suzuki-Miyaura coupling is a great topic of interest for organic chemists over the last few decades. But, the mitigation of halogen waste is the major environmental concern associated with the traditional Suzuki coupling reaction. In this concern, various abundant and cheap electrophiles such as carboxylic acid derivatives, phenol derivatives, and amides have a remarkable priority in replacing the organic halides. In this strategy, the core C-O and C-N bonds were activated to form the C-C coupling products. Based on the advantages of Ni-catalysis, the research is directed towards exploring the various Ni-based catalytic systems for the successful Suzuki coupling reaction by activating C-O and C-N bonds. The recent reports are highly motivated toward green metrics. In the current review, we would like to summarize the recent advances in the Nicatalyzed Suzuki coupling via C-O and C-N bond activation.
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页数:19
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共 103 条
  • [1] N2Phos - an easily made, highly effective ligand designed for ppm level Pd-catalyzed Suzuki-Miyaura cross couplings in water
    Akporji, Nnamdi
    Thakore, Ruchita R.
    Cortes-Clerget, Margery
    Andersen, Joel
    Landstrom, Evan
    Aue, Donald H.
    Gallou, Fabrice
    Lipshutz, Bruce H.
    [J]. CHEMICAL SCIENCE, 2020, 11 (20) : 5205 - 5212
  • [2] Mechanistic Origin of Antagonist Effects of Usual Anionic Bases (OH-, CO32-) as Modulated by their Countercations (Na+, Cs+, K+) in Palladium-Catalyzed Suzuki-Miyaura Reactions
    Amatore, Christian
    Jutand, Anny
    Le Duc, Gaetan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (21) : 6616 - 6625
  • [3] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
    Beletskaya, Irina P.
    Ananikov, Valentine P.
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1596 - 1636
  • [4] Blakemore D, 2016, RSC DRUG DISCOV, V52, P1
  • [5] Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis
    Boit, Timothy B.
    Bulger, Ana S.
    Dander, Jacob E.
    Garg, Neil K.
    [J]. ACS CATALYSIS, 2020, 10 (20) : 12109 - 12126
  • [6] Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides
    Boit, Timothy B.
    Weires, Nicholas A.
    Kim, Junyong
    Garg, Neil K.
    [J]. ACS CATALYSIS, 2018, 8 (02): : 1003 - 1008
  • [7] Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future
    Campeau, Louis-Charles
    Hazari, Nilay
    [J]. ORGANOMETALLICS, 2019, 38 (01) : 3 - 35
  • [8] Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions
    Cao, Zhi-Chao
    Xie, Si-Jun
    Fang, Huayi
    Shi, Zhang-Jie
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (42) : 13575 - 13579
  • [9] Recent Advances in the Palladium Catalyzed Suzuki-Miyaura Cross-Coupling Reaction in Water
    Chatterjee, Anamitra
    Ward, Thomas R.
    [J]. CATALYSIS LETTERS, 2016, 146 (04) : 820 - 840
  • [10] Ligand-Controlled Chemoselective C(acyl)-O Bond vs Caryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings
    Chatupheeraphat, Adisak
    Liao, Hsuan-Hung
    Srimontree, Watchara
    Guo, Lin
    Minenkov, Yury
    Poater, Albert
    Cavallo, Luigi
    Rueping, Magnus
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (10) : 3724 - 3735