Cs2CO3-catalyzed alkylation of indoles with trifluoromethyl ketones

被引：10
|
作者：
Liu, Xiao-Dong [1 ]
Wang, Yi [2 ]
Ma, Hai-Yan [1 ]
Xing, Chun-Hui [3 ]
Yuan, Yu [2 ]
Lu, Long [3 ]
机构：
[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China
[2] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2017年 / 73卷 / 16期
基金：
中国国家自然科学基金;
关键词：
3-Indolylmethanol; Trifluoromethyl ketone; Indole; Cesium carbonate; Alkylation; NONREARRANGED MONOTERPENOID UNIT; CATALYZED DIRECT ARYLATION; FRIEDEL-CRAFTS REACTIONS; DIELS-ALDER REACTIONS; ORGANOCATALYTIC HYDROXYALKYLATION; ULTRASONIC-IRRADIATION; EFFICIENT SYNTHESIS; CINCHONA ALKALOIDS; 3-INDOLYLMETHANOLS; ALDEHYDES;
D O I：
10.1016/j.tet.2017.03.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Cs2CO3-catalyzed alkylation reaction of indoles with trifluoromethyl ketones was presented. Both alicyclic and aromatic trifluoromethyl ketones as well as various substituted indoles are compatible with the methodology. Good to excellent yields of the corresponding trifluoromethyl substituted tertiary alcohols 2,2,2-tritrifluoro-1-(1H-indol-3-yl)-ethan-1-ols were acquired as the sole products. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2283 / 2289
页数：7
相关论文
共 50 条
  • [1] Cs2CO3-Catalyzed Synthesis of N-Sulfonyl-Substituted Allenamides
    Li Zheqi
    NATURAL PRODUCT COMMUNICATIONS, 2015, 10 (02) : 267 - 268
  • [2] Dy(OTf)3/Pybox-catalyzed enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones
    Sasaki, Shigeru
    Yamauchi, Takayasu
    Higashiyama, Kimio
    TETRAHEDRON LETTERS, 2010, 51 (17) : 2326 - 2328
  • [3] RhCl(CO)(PPh3)2 catalyzed α-alkylation of ketones with alcohols
    Wang, Rui
    Huang, Lina
    Du, Zhengyin
    Feng, Hua
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 846 : 40 - 43
  • [4] Unsymmetrical Disulfides Synthesis via Cs2CO3-Catalyzed Three-Component Reaction in Water
    Wang, Dungai
    Gao, Yuanji
    Tong, Yunli
    Xiong, Mingteng
    Liang, Xiao
    Zhu, Heping
    Pan, Yuanjiang
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (22) : 4991 - 4995
  • [5] Cs2CO3-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Thiols with Phosphonates and Arenes
    Song, Song
    Zhang, Yiqun
    Yeerlan, Adeli
    Zhu, Bencong
    Liu, Jianzhong
    Jiao, Ning
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (09) : 2487 - 2491
  • [6] Ruthenium-catalyzed direct C3 alkylation of indoles with α,β-unsaturated ketones
    Li, Shuai-Shuai
    Lin, Hui
    Zhang, Xiao-Mei
    Dong, Lin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (04) : 1254 - 1263
  • [7] The Cs2CO3-Catalyzed Reaction of 2-Oxindoles with Enones for the Preparation of Indolin-3-Ones and Their Further Transformation
    Shao, Ying
    Zeng, Yu-Mei
    Ji, Jie-Ying
    Sun, Xiao-Qiang
    Yang, Hai-Tao
    Miao, Chun-Bao
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24): : 12443 - 12450
  • [8] Intramolecular Construction of Trifluoromethyl Group by the Palladium-Catalyzed Alkylation of 2,3,3-Trifluoroallylic Carbonates with Indoles
    Hanakawa, Taisyun
    Isa, Kazuki
    Isobe, Shin-ichi
    Hoshino, Yuji
    Zhou, Biao
    Kawatsura, Motoi
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (04): : 2281 - 2287
  • [9] Diaminocyclopentadienone Ruthenium Complex Catalyzed Alkylation of Indoles and Ketones with Primary Alcohols
    Skowaisa, Steffen
    Haak, Edgar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
  • [10] Regioselective Construction of Coumarin-1,2,4-triazines via a Cs2CO3-Catalyzed [3+3] Cycloaddition Reaction
    Liu, Xuan-Yu
    Zhang, Fa-Guang
    Ma, Jun-An
    SYNLETT, 2022, 33 (11) : 1097 - 1101
12345