Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

被引：45
|
作者：
Cloutier, Melissa [1 ]
Roudias, Majdouline [1 ]
Paquin, Jean-Francois [1 ]
机构：
[1] Univ Laval, Dept Chim, PROTEO, CGCC, 1045 Ave Med, Quebec City G1V 0A6, PQ, Canada
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 10期
基金：
加拿大自然科学与工程研究理事会;
关键词：
ALPHA-TRIFLUOROMETHYLATED KETONES; FACILE SYNTHESIS; HYDROALKOXYLATION; ACID; CHEMISTRY; FLUORINE; ALKYNES; ACCESS;
D O I：
10.1021/acs.orglett.9b01379
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.
引用
收藏
页码：3866 / 3870
页数：5
相关论文
共 50 条
  • [41] Gold-catalyzed benzannulations of 2-alkenylindoles with alkynes: a protecting-group-free regioselective approach to carbazoles
    Amin, Pathan Mosim
    Wang, Weilin
    Wang, Chao
    Zhou, Junrui
    Wang, Youliang
    CHEMICAL COMMUNICATIONS, 2024, 60 (40) : 5326 - 5329
  • [42] Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes
    Campeau, Dominic
    Rayo, David F. Leon
    Mansour, Ali
    Muratov, Karim
    Gagosz, Fabien
    CHEMICAL REVIEWS, 2021, 121 (14) : 8756 - 8867
  • [43] Gold-Catalyzed Hydrofluorination of Internal Alkynes Using Aqueous HF
    Gauthier, Raphael
    Mamone, Marius
    Paquin, Jean-Francois
    ORGANIC LETTERS, 2019, 21 (22) : 9024 - 9027
  • [44] Gold-Catalyzed 1,2-Dicarbofunctionalization of Alkynes with Organohalides
    Sancheti, Shashank P.
    Singh, Yukta
    Mane, Manoj V.
    Patil, Nitin T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (42)
  • [45] On-surface gold-catalyzed hydroamination/cyclization reaction of alkynes
    Jimenez-Martin, Alejandro
    Munteanu, Tatiana
    Chen, Qifan
    Pascal, Simon
    Tintaru, Aura
    Mallada, Benjamin
    Mutombo, Pingo
    Siri, Olivier
    Jelinek, Pavel
    de la Torre, Bruno
    MATERIALS CHEMISTRY FRONTIERS, 2025, 9 (05) : 838 - 846
  • [46] Gold-Catalyzed Cascade Reactions of Alkynes for Construction of Polycyclic Compounds
    Ohno, Hiroaki
    ISRAEL JOURNAL OF CHEMISTRY, 2013, 53 (11-12) : 869 - 882
  • [47] Gold-Catalyzed Partial Hydrogenation of Activated Alkynes Mediated by Triphenylphosphine
    Patricia Cocoletzi-Xochitiotzi, Ana
    Hernandez-Hernandez, Miguel
    Medina-Mercado, Ignacio
    de Jesus Jimenez-Martinez, Williams
    Maricela Mastranzo, Virginia
    Porcel, Susana
    SYNTHESIS-STUTTGART, 2020, 52 (16): : 2379 - 2386
  • [48] 1,3-Dipolar Cycloaddition of SF5-Alkynes with Nonstabilized Diazo: Synthesis of Highly Substituted SF5-3H-Pyrazoles
    Peyrical, Lauriane C.
    Vinet, Laurent
    Azek, Emna
    Charette, Andre B.
    ORGANIC LETTERS, 2024, 26 (48) : 10414 - 10418
  • [49] Experimental and computational evidence on gold-catalyzed regioselective hydration of phthalimido-protected propargylamines: an entry to β-amino ketones
    Marsicano, Vincenzo
    Arcadi, Antonio
    Aschi, Massimiliano
    Michelet, Veronique
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (46) : 9438 - 9447
  • [50] Flexible Gold-Catalyzed Regioselective Oxidative Difunctionalization of Unactivated Alkenes
    de Haro, Teresa
    Nevado, Cristina
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (04) : 906 - 910
12345