Exploiting the inductive effect of the trifluoromethyl group: regioselective gold-catalyzed hydration of 2,2,2-trifluoroethyl-substituted alkynes

被引：3
|
作者：
Gauthier, Raphael [1 ]
Tzouras, Nikolaos V. [2 ,3 ]
Nolan, Steven P. [2 ,3 ]
Paquin, Jean-Francois [1 ]
机构：
[1] Univ Laval, Dept Chim, PROTEO, CCVC, 1045 Ave Med, Quebec City, PQ G1V 0A6, Canada
[2] Univ Ghent, Dept Chem, Krijgslaan 281,S-3, B-9000 Ghent, Belgium
[3] Univ Ghent, Ctr Sustainable Chem, Krijgslaan 281,S-3, B-9000 Ghent, Belgium
来源：
CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 59期
关键词：
D O I：
10.1039/d3cc02034g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The gold-catalyzed hydration of 2,2,2-trifluoroethyl-substituted alkynes is highly regioselective, producing & beta;-trifluoromethylketones as major products. This transformation illustrates the strong directing effect of the trifluoromethyl group, through its inductive effect, in gold-catalyzed addition to alkynes.
引用
收藏
页码：9138 / 9141
页数：4
相关论文
共 50 条
  • [21] An efficient synthesis of 2-trifluoromethyl quinolines via gold-catalyzed cyclization of trifluoromethylated propargylamines
    Zhu, Mei
    Fu, Weijun
    Zou, Guanglong
    Xun, Chen
    Deng, Dongsheng
    Ji, Baoming
    JOURNAL OF FLUORINE CHEMISTRY, 2012, 135 : 195 - 199
  • [22] Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by a Neighboring Carbonyl Group: Access to α-Acyloxy Methyl Ketones and Synthesis of (±)-Actinopolymorphol B
    Ghosh, Nayan
    Nayak, Sanatan
    Sahoo, Akhila K.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02): : 500 - 511
  • [23] Nanoporous Gold-Catalyzed [4+2] Benzannulation between ortho-Alkynylbenzaldehydes and Alkynes
    Asao, Naoki
    Menggenbateer
    Seya, Yohei
    Yamamoto, Yoshinori
    Chen, Mingwei
    Zhang, Wei
    Inoue, Akihisa
    SYNLETT, 2012, 23 (01) : 66 - 69
  • [24] Et3N-Catalyzed Cycloaddition Reactions of α-(Trifluoromethyl)styrenes with 2,2,2-Trifluorodiazoethane to Access Bis(trifluoromethyl)-Substituted Pyrazolines
    Li, Chunmei
    Zhang, Xuxue
    He, Jingjing
    Xu, Sixue
    Cao, Song
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (02) : 301 - 306
  • [25] Gold-Catalyzed Fluorination-Hydration: Synthesis of -Fluorobenzofuranones from 2-Alkynylphenol Derivatives
    Wang, Qiang
    Jiang, Yu
    Sun, Run
    Tang, Xiang-Ying
    Shi, Min
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (41) : 14739 - 14745
  • [26] Convergent Synthesis of 2-Aryl-Substituted Quinolines by Gold-Catalyzed Cascade Reaction
    Ueda, Hirofumi
    Yamaguchi, Minami
    Tokuyama, Hidetoshi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2016, 64 (07) : 824 - 829
  • [27] 2,3-Difunctionalization of quinones: a gold-catalyzed cascade approach for trifluoromethyl-amination or sulfoximination
    Sharma, Alpa
    Govande, Vijaya
    Mahajan, Shivangani
    Sawant, Sanghapal D.
    CHEMICAL COMMUNICATIONS, 2024, 60 (71) : 9598 - 9601
  • [28] Gold-catalyzed formal (3+2) and (4+2) cycloadditions of alkynes to highly functionalized dihydropyrroles and tetrahydropyridines
    Zhang, Xiao-Qian
    Xu, Tianyi
    Zhang, Congdi
    Wang, Chao
    Wang, Youliang
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (03) : 680 - 685
  • [29] Catalytic Asymmetric Synthesis of Vicinally Bis(trifluoromethyl)-Substituted Molecules via Normal [3+2] Cycloaddition of N-2,2,2-Trifluoroethyl Benzothiophene Ketimines and β-Trifluoromethyl Enones
    Zhao, Jian-Qiang
    Zhang, Xue-Man
    He, Yu-Ying
    Peng, Qiao-Qiao
    Rao, Han-Wen
    Zhang, Yan-Ping
    Wang, Zhen-Hua
    You, Yong
    Yuan, Wei-Cheng
    ORGANIC LETTERS, 2023, 25 (44) : 8027 - 8032
  • [30] Access to Quinolines through Gold-Catalyzed Intermolecular Cycloaddition of 2-Aminoaryl Carbonyls and Internal Alkynes
    Cai, Shuting
    Zeng, Jing
    Bai, Yaguang
    Liu, Xue-Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 801 - 807
12345