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
  • [21] Cu-catalyzed reductive Friedel-Crafts alkylation of indoles with ketones for one-pot synthesis of 3-substituted indoles
    Wang, Wengang
    Mao, Zewei
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2025, 1027
  • [22] Oxazaborolidinone-Catalyzed Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with α,β-Unsaturated Ketones
    Adachi, Shinya
    Tanaka, Fumi
    Watanabe, Kazuya
    Harada, Toshiro
    ORGANIC LETTERS, 2009, 11 (22) : 5206 - 5209
  • [23] Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with Simple α,β-Unsaturated Ketones Catalyzed by Oxazaborolidinone
    Adachi, Shinya
    Tanaka, Fumi
    Watanabe, Kazuya
    Watada, Atsushi
    Harada, Toshiro
    SYNTHESIS-STUTTGART, 2010, (15): : 2652 - 2669
  • [24] Synthesis of 1,3-Disubstituted Symmetrical/Unsymmetrical Ureas via Cs2CO3-Catalyzed Transamination of Ethylene Carbonate and Primary Amines
    Jagtap, Sachin R.
    Patil, Yogesh P.
    Panda, Anil G.
    Bhanage, Bhalchandra M.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (12) : 2093 - 2100
  • [25] An expedient synthesis of 3-substituted indoles via reductive alkylation with ketones
    Rizzo, John R.
    Alt, Charles A.
    Zhang, Tony Y.
    TETRAHEDRON LETTERS, 2008, 49 (48) : 6749 - 6751
  • [26] First example of FeCl3-catalyzed alkylation of indoles with pinenes
    Yadav, J. S.
    Reddy, B. V. Subba
    Narasimhulu, G.
    Reddy, N. Sivasankar
    Reddy, P. Narayana
    Purnima, K. V.
    Naresh, P.
    Jagadeesh, B.
    TETRAHEDRON LETTERS, 2010, 51 (02) : 244 - 247
  • [27] Friedel-Crafts Alkylation of Indoles with Aldehydes/Ketones Catalyzed by Bromodiarylethene-Based Photoacid Generators
    Zakharov, Alexey V.
    Timofeeva, Sofia M.
    Shirinian, Valerii Z.
    SYNTHESIS-STUTTGART, 2024, 56 (14): : 2247 - 2258
  • [28] Synthesis of 3-phenylsulfonyl-2-trifluoromethyl-1H-indoles: A copper catalyzed cyclization approach
    Lopez, Simon E.
    Gallagher, Reese
    Gilliland, Robert J.
    Ghiviriga, Ion
    Dolbier, William R., Jr.
    JOURNAL OF FLUORINE CHEMISTRY, 2017, 193 : 118 - 125
  • [29] Sc(OTf)3-catalyzed alkylation of indoles with propargyl alcohols:: an expeditious synthesis of 3-substituted indoles
    Yadav, J. S.
    Reddy, B. V. Subba
    Rao, K. V. Raghavendra
    Kumar, G. G. K. S. Narayana
    TETRAHEDRON LETTERS, 2007, 48 (31) : 5573 - 5576
  • [30] In(III)-catalyzed C3-alkylation of indoles with 2H-chromen-2-ol derivatives
    Kaushal, Anjali
    Bhukya, Jagadeesh
    Yadav, Ashok Kumar
    Mishra, Vivek
    Kumar, Deepak
    TETRAHEDRON LETTERS, 2023, 129
12345