Palladium-catalyzed difluorocarbene transfer synthesis of diaryl ketones from iodoarene and arylboronic acid

被引:0
|
作者
Tan, Zhiyong [1 ]
Chen, Tingting [1 ]
Shen, Jiayi [1 ]
Zhu, Jinbin [1 ]
Zhong, Weihong [2 ]
Guo, Wei [1 ]
机构
[1] Gannan Normal Univ, Jiangxi Prov Key Lab Synthet Pharmaceut Chem, Ganzhou 341000, Peoples R China
[2] Jiangxi Univ Chinese Med, Nanchang 330004, Peoples R China
基金
中国国家自然科学基金;
关键词
TRANSFER ENABLES ACCESS; ARYL HALIDES; FACILE SYNTHESIS; CARBONYLATION; COMPLEXES;
D O I
10.1039/d4qo02405b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we disclose a novel carbonylative Suzuki-Miyaura reaction for the synthesis of diaryl ketones via palladium-catalyzed difluorocarbene transfer. BrCF2CO2Et was employed as a safe and effective carbonyl surrogate. CO was readily in situ generated from the reaction of H2O with intermediate PdII 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 CF2. The current protocol offers a pragmatic and efficient approach for the synthesis of a series of diaryl ketones with yields of up to 97%. The broad substrate scope and further synthetic applications in drugs and functional compounds indicate that this carbonylative reaction is a highly appealing strategy.
引用
收藏
页数:7
相关论文
共 50 条
  • [31] Palladium-catalyzed fluoroacylation of (Hetero)arylboronic acid with fluorothioacetates at ambient temperature
    Yi, Xing
    Cao, Ya-Fang
    Wang, Xing
    Xu, Hui
    Ban, Shu-Rong
    Dai, Hui-Xiong
    TETRAHEDRON LETTERS, 2020, 61 (16)
  • [32] Palladium-Catalyzed Cascade Reactions of δ-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines
    Yao, Xinrong
    Qi, Linjun
    Li, Renhao
    Zhen, Qanqian
    Liu, Jichao
    Zhao, Zhiwei
    Shao, Yinlin
    Hu, Maolin
    Chen, Jiuxi
    ACS COMBINATORIAL SCIENCE, 2020, 22 (03) : 114 - 119
  • [33] Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids
    DeBergh, J. Robb
    Niljianskul, Nootaree
    Buchwald, Stephen L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) : 10638 - 10641
  • [34] An atom-efficient palladium-catalyzed cross-coupling reaction of triarylbismuths with acid chlorides: synthesis of diaryl and alkyl aryl ketones
    Rao, Maddah L. N.
    Venkatesh, Varadhachari
    Jadhav, Deepak N.
    TETRAHEDRON LETTERS, 2006, 47 (39) : 6975 - 6978
  • [35] Palladium-catalyzed hydroarylation of alkynes with arylboronic acids
    Xu, Xiaoling
    Chen, Jiuxi
    Gao, Wenxia
    Wu, Huayue
    Ding, Jinchang
    Su, Weike
    TETRAHEDRON, 2010, 66 (13) : 2433 - 2438
  • [36] Palladium-Catalyzed Amide Synthesis via Aminocarbonylation of Arylboronic Acids with Nitroarenes
    Peng, Jin-Bao
    Li, Da
    Geng, Hui-Qing
    Wu, Xiao-Feng
    ORGANIC LETTERS, 2019, 21 (12) : 4878 - 4881
  • [37] Palladium-Catalyzed Acid Chloride Synthesis
    Kikuchi, Jun
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2018, 76 (07) : 730 - 731
  • [38] Palladium-Catalyzed Synthesis of Diaryl Ketones from Aldehydes and (Hetero)Aryl Halides via C-H Bond Activation
    Wakaki, Takayuki
    Togo, Takaya
    Yoshidome, Daisuke
    Kuninobu, Yoichiro
    Kanai, Motomu
    ACS CATALYSIS, 2018, 8 (04): : 3123 - +
  • [39] Palladium-catalyzed addition of arylboronic acids to isocyanates
    Kianmehr, Ebrahim
    Rajabi, Azam
    Ghanbari, Mohammad
    TETRAHEDRON LETTERS, 2009, 50 (15) : 1687 - 1688
  • [40] Palladium-catalyzed addition of arylboronic acids to aldehydes
    Yamamoto, T
    Ohta, T
    Ito, Y
    ORGANIC LETTERS, 2005, 7 (19) : 4153 - 4155