Suzuki-Miyaura Coupling of Aryl Iodides, Bromides, and Chlorides Catalyzed by Bis(thiazole) Pincer Palladium Complexes

被引:39
|
作者
Luo, Qun-Li [1 ]
Tan, Jian-Ping [1 ]
Li, Zhi-Fu [1 ]
Nan, Wen-Hui [1 ]
Xiao, Dong-Rong [1 ]
机构
[1] Southwest Univ, Coll Chem & Chem Engn, Chongqing 400715, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 18期
关键词
PALLADACYCLES; PRECURSOR; PYRIDINE; LIGANDS;
D O I
10.1021/jo3011733
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bis(thiazole) pincer palladium complexes showed efficient catalytic activity for the Suzuki-Miyaura coupling of aryl halides, allowing the synthesis of biaryls with very high turnover numbers and turnover frequencies. The complexes were successfully applied in the scalable and green synthesis of the key intermediates of bioactive LUF5771 and its analogues.
引用
收藏
页码:8332 / 8337
页数:6
相关论文
共 50 条
  • [1] Suzuki-Miyaura cross-coupling reaction of aryl bromides catalyzed by palladium(II) pyridoxal hydrazone complexes
    Pandiarajan, Devaraj
    Ramesh, Rengan
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 708 : 18 - 24
  • [2] Bis-benzimidazolium-palladium system catalyzed Suzuki-Miyaura coupling reaction of aryl bromides under mild conditions
    Lin, Yi-Rang
    Chiu, Chien-Cheng
    Chiu, Huai-Tsu
    Lee, Dong-Sheng
    Lu, Ta-Jung
    APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (01)
  • [3] Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters
    Ben Halima, Taoufik
    Zhang, Wanying
    Yalaoui, Imane
    Hong, Xin
    Yang, Yun-Fang
    Houk, Kendall N.
    Newman, Stephen G.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) : 1311 - 1318
  • [4] Palladium-Catalyzed Suzuki-Miyaura Coupling Reactions of Boronic Acid Derivatives with Aryl Chlorides
    Zhou, Zihong
    Zhang, Yaqi
    Xia, Wang
    Chen, Huixuan
    Liang, Hao
    He, Xuefeng
    Yu, Sifan
    Cao, Rihui
    Qiu, Liqin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (10) : 1260 - 1268
  • [5] Suzuki-Miyaura cross-coupling reaction of aryl bromides and chlorides with phenylboronic acid under aerobic conditions catalyzed by palladium complexes with thiosemicarbazone ligands
    Kostas, ID
    Andreadaki, FJ
    Kovala-Demertzi, D
    Prentjas, C
    Demertzis, MA
    TETRAHEDRON LETTERS, 2005, 46 (12) : 1967 - 1970
  • [6] Palladium-Catalyzed Coupling of Hydroxylamines with Aryl Bromides, Chlorides, and Iodides
    Porzelle, Achim
    Woodrow, Michael D.
    Tomkinson, Nicholas C. O.
    ORGANIC LETTERS, 2009, 11 (01) : 233 - 236
  • [7] An Easily Prepared Tetraphosphine and Its Use in the Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Chlorides
    Wang, Kun
    Wang, Wei
    Luo, Heng
    Zheng, Xueli
    Fu, Haiyan
    Chen, Hua
    Li, Ruixiang
    CATALYSIS LETTERS, 2013, 143 (11) : 1214 - 1219
  • [8] Bioactive NHC-derived palladium complexes: synthesis, catalytic activity for the Suzuki-Miyaura coupling of aryl chlorides and bromides and their antibacterial activities
    Boubakri, Lamia
    Al-Ayed, Abdullah S.
    Mansour, L.
    Abutaha, Nael
    Harrath, Abdel Halim
    Ozdemir, I
    Yasar, S.
    Hamdi, Naceur
    JOURNAL OF COORDINATION CHEMISTRY, 2019, 72 (16) : 2688 - 2704
  • [9] A functionalized phosphine ligand with a pentaarylbenzene moiety in palladium-catalyzed Suzuki-Miyaura coupling of aryl chlorides
    Iwasawa, Tetsuo
    Kamei, Toshinori
    Watanabe, Satoshi
    Nishiuchi, Masaki
    Kawamura, Yasuhiko
    TETRAHEDRON LETTERS, 2008, 49 (52) : 7430 - 7433
  • [10] A General Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Mesylates
    So, Chau Ming
    Lau, Chak Po
    Kwong, Fuk Yee
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8059 - 8063