Palladium-catalyzed Suzuki-Miyaura cross-coupling of carboxylic-phosphoric anhydrides via C-O bond cleavage

被引:0
|
作者
Ji, Haiyao [1 ]
Ma, Yilin [1 ]
Zhang, Jianwen [1 ]
Xing, Feifei [1 ]
Liu, Chengwei [1 ]
机构
[1] Shanghai Univ, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China
关键词
KETONE SYNTHESIS; AMIDES; BIARYLS; ACIDS; EFFICIENT; HALIDES; ESTERS;
D O I
10.1039/d4ob00548a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A robust palladium-catalyzed Suzuki-Miyaura reaction of carboxylic-phosphoric anhydrides via highly selective C(O)-O bond cleavage under inorganic base-free conditions has been reported. Carboxylic-phosphoric anhydrides, generated through activating carboxylic acids using phosphates by esterification or direct dehydrogenative reaction with phosphites, have been employed as highly reactive electrophiles for Suzuki-Miyaura cross-coupling reactions. Broad substrate scope and excellent functional group tolerance have been demonstrated to be a general and practical approach for the synthesis of highly valuable ketones.
引用
收藏
页码:5578 / 5584
页数:7
相关论文
共 50 条
  • [21] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands
    Martin, Ruben
    Buchwald, Stephen L.
    ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1461 - 1473
  • [22] Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates
    Molander, GA
    Biolatto, B
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11): : 4302 - 4314
  • [23] Efficient Pyrimidone-Promoted Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction
    Zhang, Hong-Ping
    Dai, You-Zhi
    Zhou, Xi
    Yu, Huang
    SYNLETT, 2012, (08) : 1221 - 1224
  • [24] Palladium-catalyzed oxidative C-O cross-coupling of ketene dithioacetals and carboxylic acids
    Liang, Deqiang
    Wang, Mang
    Dong, Ying
    Guo, Yaru
    Liu, Qun
    RSC ADVANCES, 2014, 4 (13): : 6564 - 6567
  • [25] Bis-isocyanide Palladium catalyzed Suzuki-Miyaura cross-coupling
    Stauber, Julia M.
    Figueroa, Joshua S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [26] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of N-Mesylamides by N-C Cleavage: Electronic Effect of the Mesyl Group
    Liu, Chengwei
    Liu, Yongmei
    Liu, Ruzhang
    Lalancette, Roger
    Szostak, Roman
    Szostak, Michal
    ORGANIC LETTERS, 2017, 19 (06) : 1434 - 1437
  • [27] Palladium-Catalyzed C-O Cross-Coupling of Primary Alcohols
    Zhang, Hong
    Ruiz-Castillo, Paula
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2018, 20 (06) : 1580 - 1583
  • [28] Dabco as an inexpensive and highly efficient ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction
    Li, JH
    Liu, WJ
    ORGANIC LETTERS, 2004, 6 (16) : 2809 - 2811
  • [29] Palladium-Catalyzed Synthesis of Heterocycle-Containing Diarylmethanes through Suzuki-Miyaura Cross-Coupling
    Kuriyama, Masami
    Shinozawa, Mina
    Hamaguchi, Norihisa
    Matsuo, Seira
    Onomura, Osamu
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12): : 5921 - 5928
  • [30] Monooxychlorophosphine as a novel and efficient ligand for palladium-catalyzed suzuki-miyaura cross-coupling of aryl chlorides
    Mai, Wenpeng
    Lv, Guanghua
    Gao, Lianxun
    SYNLETT, 2007, (14) : 2247 - 2251