Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides

被引:35
|
作者
Zhou, Tongliang [1 ]
Xie, Pei-Pei [2 ]
Ji, Chong-Lei [2 ]
Hong, Xin [2 ]
Szostak, Michal [1 ]
机构
[1] Rutgers State Univ, Dept Chem, Newark, NJ 07102 USA
[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
CARBOXYLIC-ACIDS; PRECATALYSTS; ACTIVATION; COMPLEXES; KETONES; AMIDES;
D O I
10.1021/acs.orglett.0c02250
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a catalyst system for Pd-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of aroyl chlorides with boronic acids to furnish biaryls. This strategy is suitable for a broad range of common aroyl chlorides and boronic acids. The synthetic utility is highlighted in the direct late-stage functionalization of pharmaceuticals and natural products capitalizing on the presence of carboxylic acid moiety. Extensive mechanistic and DFT studies provide key insight into the reaction mechanism and high decarbonylative cross-coupling selectivity.
引用
收藏
页码:6434 / 6440
页数:7
相关论文
共 50 条
  • [1] Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides
    Dreher, Spencer D.
    Lim, Siang-Ee
    Sandrock, Deidre L.
    Molander, Gary A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3626 - 3631
  • [2] Suzuki-Miyaura Cross-Coupling of Sulfoxides
    Chen, Qianwei
    Wu, Shufeng
    Yan, Shuqin
    Li, Chengxi
    Abduhulam, Hayrul
    Shi, Yanhui
    Dang, Yanfeng
    Cao, Changsheng
    [J]. ACS CATALYSIS, 2020, 10 (15) : 8168 - 8176
  • [3] Suzuki-Miyaura Cross-Coupling of Potassium Dioxolanylethyltrifluoroborate and Aryl/Heteroaryl Chlorides
    Fleury-Bregeot, Nicolas
    Oehlrich, Daniel
    Rombouts, Frederik
    Molander, Gary A.
    [J]. ORGANIC LETTERS, 2013, 15 (07) : 1536 - 1539
  • [4] Biaryl Ketones by Suzuki-Miyaura Cross-Coupling of Organotrifluoroborates and Acyl Chlorides
    Forbes, Alaina M.
    Meier, G. Patrick
    Jones-Mensah, Ebenezer
    Magolan, Jakob
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (17) : 2983 - 2987
  • [5] Synthesis of Triazole Click Ligands for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides
    Jabeen, S.
    Khera, R. A.
    Iqbal, J.
    Asgher, M.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (09) : 1416 - 1422
  • [6] Synthesis of Triazole Click Ligands for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides
    S. Jabeen
    R. A. Khera
    J. Iqbal
    M. Asgher
    [J]. Russian Journal of Organic Chemistry, 2019, 55 : 1416 - 1422
  • [7] Suzuki-Miyaura cross-coupling of potassium trifluoroboratohomoenolates
    Molander, Gary A.
    Petrillo, Daniel E.
    [J]. ORGANIC LETTERS, 2008, 10 (09) : 1795 - 1798
  • [8] Mechanochemical Synthesis of Ketones via Chemoselective Suzuki-Miyaura Cross-Coupling of Acyl Chlorides
    Zhang, Jin
    Zhang, Pei
    Ma, Yangmin
    Szostak, Michal
    [J]. ORGANIC LETTERS, 2022, 24 (12) : 2338 - 2343
  • [9] Synthesis of Biaryls via Decarbonylative Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Aryl Anhydrides
    Zhou, Jing-Ya
    Liu, Rui-Qing
    Wang, Cheng-Yi
    Zhu, Yong-Ming
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (21): : 14149 - 14157
  • [10] Synthesis of Biaryls via Decarbonylative Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Carboxylic Acids
    Liu, Chengwei
    Ji, Chong-Lei
    Qin, Zhi-Xin
    Hong, Xin
    Szostak, Michal
    [J]. ISCIENCE, 2019, 19 : 749 - +