Cu-Mediated Chemoselective Trifluoromethylation of Benzyl Bromides Using Shelf-Stable Electrophilic Trifluoromethylating Reagents

被引：109

作者：

Kawai, Hiroyuki ^{[1
]}

Furukawa, Tatsuya ^{[1
]}

Nomura, Yoshinori ^{[1
]}

Tokunaga, Etsuko ^{[1
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 14期

关键词：

CATALYZED TRIFLUOROMETHYLATION; ENANTIOSELECTIVE TRIFLUOROMETHYLATION; ORGANIC HALIDES; NUCLEOPHILIC TRIFLUOROMETHYLATION; CONFIGURATIONAL STABILITY; REDUCTIVE ELIMINATION; MEDICINAL CHEMISTRY; CONVENIENT METHOD; BORONIC ACIDS; SALT SYSTEM;

D O I：

10.1021/ol201205t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper-mediated chemoselective trifluoromethylation at the benzylic :position by the use of shelf-stable electrophilic trifluoromethylating reagents 3 in good to high yields under mild conditions is described for the first time. The generality of this trifluoromethylation for a wide variety of benzyl bromides facilitates the rapid creation of structural diversity of medicinal candidates in drug discovery.

引用

页码：3596 / 3599

页数：4

共 90 条

[21] Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent
Kieltsch, Iris
Eisenberger, Patrick
Togni, Antonio
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (05) : 754 - 757
[22] The first Cu(I)-mediated nucleophilic trifluoromethylation reactions using (trifluoromethyl)trimethylsilane in ionic liquids
Kim, J
Shreeve, JM
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) : 2728 - 2734
[23] Kirsch P., 2013, Modern Fluoroorganic Chemistry
[24] Design and Synthesis of Phthalimide-Based Fluorescent Liver X Receptor Antagonists
Kishida, Kenji
Aoyama, Atsushi
Hashimoto, Yuichi
Miyachi, Hiroyuki
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (11) : 1525 - 1528
[25] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS BETWEEN ALLYL, VINYL OR ARYL HALIDE AND PERFLUOROALKYL IODIDE WITH ZINC AND ULTRASONIC IRRADIATION
KITAZUME, T
ISHIKAWA, N
[J]. CHEMISTRY LETTERS, 1982, (01) : 137 - 140
[26] Copper-Catalyzed Trifluoromethylation of Aryl Iodides with Potassium (Trifluoromethyl)trimethoxyborate
Knauber, Thomas
Arikan, Fatih
Roeschenthaler, Gerd-Volker
Goossen, Lukas J.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (09) : 2689 - 2697
[27] KOBAYASHI Y, 1969, TETRAHEDRON LETT, P4095
[28] KOBAYASHI Y, 1979, TETRAHEDRON LETT, P4071
[29] Zinc-Mediated Formation of Trifluoromethyl Ethers from Alcohols and Hypervalent Iodine Trifluoromethylation Reagents
Koller, Raffael
Stanek, Kyrill
Stolz, Daniel
Aardoom, Raphael
Niedermann, Katrin
Togni, Antonio
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) : 4332 - 4336
[30] KONDRATENKO NV, 1980, SYNTHESIS-STUTTGART, P932

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