Synthesis of Arylstannanes via Palladium-Catalyzed Decarbonylative Coupling of Aroyl Fluorides

被引:30
|
作者
Kayumov, Muzaffar [1 ,2 ]
Zhao, Jian-Nan [1 ,3 ]
Mirzaakhmedov, Sharafitdin [4 ]
Wang, Dong-Yu [1 ]
Zhang, Ao [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, SIMM, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai 201210, Peoples R China
[4] Acad Sci Uzbek, Inst Bioorgan Chem, Tashkent 100125, Uzbekistan
基金
中国国家自然科学基金;
关键词
stannylation; Pd-catalyzed; acyl fluorides; decarbonylation; late-stage diversification; ARYL STANNANES; MEDIATED FLUORINATION; ACID FLUORIDES; HALIDES; STANNYLATION; REAGENTS;
D O I
10.1002/adsc.201901223
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Aryl stannanes are valuable precursors in organic transformations, but their synthetic methods are limited. Here we present a Pd-catalyzed decarbonylative stannylation of acid fluorides in the absence of exogenous base. Various aryl stannanes were efficiently prepared from bench-stable transition metal catalyst and ligand with broad functional group compatibility and substrate scope including natural products and pharmaceuticals. This protocol was also successfully used to a late-stage diversification of an existing uricosuric drug probenecid
引用
收藏
页码:776 / 781
页数:6
相关论文
共 50 条
  • [1] Palladium-Catalyzed Decarbonylative Alkylation of Acyl Fluorides
    Fu, Liyan
    Chen, Qiang
    Wang, Zhenhua
    Nishihara, Yasushi
    ORGANIC LETTERS, 2020, 22 (06) : 2350 - 2353
  • [2] Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides
    Keaveney, Sinead T.
    Schoenebeck, Franziska
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (15) : 4073 - 4077
  • [3] Palladium-catalyzed Decarbonylative Cyanation of Acyl Fluorides and Chlorides
    Sakurai, Shun
    Tobisu, Mamoru
    CHEMISTRY LETTERS, 2021, 50 (01) : 151 - 153
  • [4] PALLADIUM-CATALYZED COUPLING OF ALLYLIC ACETATES WITH ARYLSTANNANES AND VINYLSTANNANES
    DELVALLE, L
    STILLE, JK
    HEGEDUS, LS
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10): : 3019 - 3023
  • [5] Synthesis of Amides by Palladium-Catalyzed Decarbonylative Coupling of Carboxylic Acids with Isocyanides
    Huang, Lin
    Guo, Haili
    Pan, Lingxia
    Xie, Chunsong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (27) : 6027 - 6031
  • [6] Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes
    Lian, Chang
    Yue, Guanglu
    Zhang, Haonan
    Wei, Liyan
    Liu, Danyang
    Liu, Sichen
    Fang, Huayi
    Qiu, Di
    TETRAHEDRON LETTERS, 2018, 59 (45) : 4019 - 4023
  • [7] PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY
    FARINA, V
    KRISHNAN, B
    MARSHALL, DR
    ROTH, GP
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20): : 5434 - 5444
  • [8] Synthesis of ikimine a via palladium-catalyzed coupling
    Larock, RC
    Dong, XY
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 288 - ORGN
  • [9] Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions
    Kubo, Masayuki
    Inayama, Naomi
    Ota, Eisuke
    Yamaguchi, Junichiro
    ORGANIC LETTERS, 2022, 24 (21) : 3855 - 3860
  • [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
    ISCIENCE, 2019, 19 : 749 - +