Zinc-Mediated Formation of Trifluoromethyl Ethers from Alcohols and Hypervalent Iodine Trifluoromethylation Reagents

被引:261
作者
Koller, Raffael [1 ]
Stanek, Kyrill [1 ]
Stolz, Daniel [1 ]
Aardoom, Raphael [1 ]
Niedermann, Katrin [1 ]
Togni, Antonio [1 ]
机构
[1] ETH, Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland
关键词
etherification; synthetic methods; hypervalent compounds; iodine; trifluoromethylation; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; MEDICINAL CHEMISTRY; SALTS; FLUORINE; ACIDS; FLUOROALKYLATION; SPECTROSCOPY; DIFFUSION; RILUZOLE; AGENTS;
D O I
10.1002/anie.200900974
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A (fluor)ry of activity: The transfer of an intact trifluoromethyl group from a hypervalent iodine reagent to an aliphatic alcohol occurs smoothly upon activation by zinc bis(triflimide). This constitutes a straightforward method for the preparation of trifluoromethoxy alkyl derivatives, compounds otherwise difficult to access. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4332 / 4336
页数:5
相关论文
共 42 条
  • [1] Riluzole augmentation in treatment-resistant obsessive-compulsive disorder: An open-label trial
    Coric, V
    Taskiran, S
    Pittenger, C
    Wasylink, S
    Mathalon, DH
    Valentine, G
    Saksa, J
    Wu, YT
    Gueorguieva, R
    Sanacora, R
    Malison, RT
    Krystal, JH
    [J]. BIOLOGICAL PSYCHIATRY, 2005, 58 (05) : 424 - 428
  • [2] Clinical studies of riluzole in amyotrophic lateral sclerosis
    Desai, J
    Swash, M
    [J]. DRUGS OF TODAY, 1997, 33 (08) : 595 - 600
  • [3] The first fluoroalkylation of amino acids and peptides in water utilizing the novel iodonium salt (CF3SO2)2NI(Ph)CH2CF3
    DesMarteau, DD
    Montanari, V
    [J]. CHEMICAL COMMUNICATIONS, 1998, (20) : 2241 - 2242
  • [4] Versatile direct dehydrative approach for diaryliodonium(III) salts in fluoroalcohol media
    Dohi, Toshifumi
    Ito, Motoki
    Morimoto, Koji
    Minamitsuji, Yutaka
    Takenaga, Naoko
    Kita, Yasuyuki
    [J]. CHEMICAL COMMUNICATIONS, 2007, (40) : 4152 - 4154
  • [5] Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation
    Eisenberger, P
    Gischig, S
    Togni, A
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) : 2579 - 2586
  • [6] Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(III)-CF3 reagents
    Eisenberger, Patrick
    Kieltsch, Iris
    Armanino, Nicolas
    Togni, Antonio
    [J]. CHEMICAL COMMUNICATIONS, 2008, (13) : 1575 - 1577
  • [7] CHEMISTRY IN HYDROGEN-FLUORIDE .7. NOVEL SYNTHESIS OF ARYL TRIFLUOROMETHYL ETHERS
    FEIRING, AE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (16) : 2907 - 2910
  • [8] Cyclic diaryliodonium ions: old mysteries solved and new applications envisaged
    Grushin, VV
    [J]. CHEMICAL SOCIETY REVIEWS, 2000, 29 (05) : 315 - 324
  • [9] Fluorine in medicinal chemistry: A review of anti-cancer agents
    Isanbor, C
    O'Hagan, D
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (03) : 303 - 319
  • [10] A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithio carbonates
    Kanie, K
    Tanaka, Y
    Suzuki, K
    Kuroboshi, M
    Hiyama, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (02) : 471 - 484