N-Acylsuccinimides: Efficient acylative coupling reagents in palladium-catalyzed Suzuki coupling via C-N cleavage

被引：40
|
作者：
Cui, Ming [1 ]
Chen, Zeyu [2 ]
Liu, Tingting [1 ]
Wang, Hui [1 ]
Zeng, Zhuo [1 ,3 ]
机构：
[1] South China Normal Univ, Coll Chem & Environm, Guangzhou 510006, Guangdong, Peoples R China
[2] Xishuangbanna Entry Exit Inspect & Quarantine Bur, Jinghong 666100, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 LingLing Rd, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 40期
基金：
中国国家自然科学基金;
关键词：
Amide C-N bond cleavage; N-Acylsuccinimides; Diaryl ketones; Acylative Suzuki coupling; High atom utilization; CARBOXYLIC ANHYDRIDES; ARYLBORONIC ACIDS; TWISTED AMIDES; ORGANOBORON COMPOUNDS; ROTATIONAL PATHWAY; KETONE SYNTHESIS; ACYL CHLORIDES; ESTERS; ACYLSACCHARINS; ACTIVATION;
D O I：
10.1016/j.tetlet.2017.08.044
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An acylative Suzuki coupling of activated amides with aryl boronic acids has been reported via palladium-catalyzed C-N bond cleavage. This protocol demonstrate amides can be activated by an atom-economic and cheap succinimide, which can be efficiently utilized to synthesize broad array of diaryl ketones in moderate to good yields. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3819 / 3822
页数：4
相关论文
共 50 条
  • [31] Stille coupling via C-N bond cleavage
    Wang, Dong-Yu
    Kawahata, Masatoshi
    Yang, Ze-Kun
    Miyamoto, Kazunori
    Komagawa, Shinsuke
    Yamaguchi, Kentaro
    Wang, Chao
    Uchiyama, Masanobu
    [J]. NATURE COMMUNICATIONS, 2016, 7
  • [32] Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles
    Arthuis, Martin
    Pontikis, Renee
    Florent, Jean-Claude
    [J]. ORGANIC LETTERS, 2009, 11 (20) : 4608 - 4611
  • [33] Palladium-Catalyzed Hydroaminocarbonylation of Alkynes with Tertiary Amines via C-N Bond Cleavage
    Gao, Bao
    Huang, Hanmin
    [J]. ORGANIC LETTERS, 2017, 19 (22) : 6260 - 6263
  • [34] Optimization of a palladium-catalyzed C-N coupling towards the robust synthesis of a RORc ligand
    Lao, David
    Sirois, Lauren
    Angelaud, Remy
    Xu, Jie
    Gosselin, Francis
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [35] Applications of palladium-catalyzed C-N cross-coupling reactions in pharmaceutical compounds
    Emadi, Reza
    Nekoo, Abbas Bahrami
    Molaverdi, Fatemeh
    Khorsandi, Zahra
    Sheibani, Reza
    Sadeghi-Aliabadi, Hojjat
    [J]. RSC ADVANCES, 2023, 13 (27) : 18715 - 18733
  • [36] Palladium-catalyzed decarbonylative C-N coupling to convert arylcarbamoyl chlorides to urea derivatives
    Fan, Aihong
    Peng, Jinsong
    Zhou, Dun
    Li, Xiang
    Chen, Chunxia
    [J]. SYNTHETIC COMMUNICATIONS, 2020, 50 (20) : 3113 - 3124
  • [37] PALLADIUM-CATALYZED COUPLING OF N-HETEROARYL SULFIDES WITH ORGANOZINC REAGENTS
    Koshiba, Takahiro
    Miyazaki, Tohru
    Tokuyama, Hidetoshi
    Fukuyama, Tohru
    [J]. HETEROCYCLES, 2009, 77 (01) : 233 - 239
  • [38] Palladium-catalyzed intramolecular C-N coupling: Facile synthesis of tetracyclic C(3)-aminoisoindolinones
    Surya Prakash Rao, H.
    Prabhakaran, J.
    [J]. SYNTHETIC COMMUNICATIONS, 2022, 52 (11-12) : 1448 - 1456
  • [39] Ruthenium-catalyzed Suzuki coupling of anilines with alkenyl borates via selective aryl C-N bond cleavage
    Xu, Jian-Xing
    Zhao, Fengqian
    Franke, Robert
    Wu, Xiao-Feng
    [J]. CATALYSIS COMMUNICATIONS, 2020, 140
  • [40] A Practical and Scalable Synthesis of a Glucokinase Activator via Diastereomeric Resolution and Palladium-Catalyzed C-N Coupling Reaction
    Yamashita, Yohei
    Morinaga, Yasuhiro
    Kasai, Makoto
    Hashimoto, Takao
    Takahama, Yuji
    Ohigashi, Atsushi
    Yonishi, Satoshi
    Akazome, Motohiro
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2017, 21 (03) : 346 - 356
12345