TBD-Catalyzed Trifluoromethylation of Carbonyl Compounds with (Trifluoromethyl)trimethylsilane

被引：12

作者：

Matsukawa, S. ^{[1
]}

Takahashi, S. ^{[1
]}

Takahashi, H. ^{[1
]}

机构：

[1] Ibaraki Univ, Fac Educ, Dept Sci Educ, Mito, Ibaraki 3108512, Japan

来源：

SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 11期

关键词：

Base catalyst; guanidine; organocatalyst; organosilicon compounds; trifluoromethylation; TRIALKYL(TRIFLUOROMETHYL)SILANES;

D O I：

10.1080/00397911.2011.644381

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trifluoromethylation of carbonyl compounds using (trifluoromethyl) trimethylsilane catalyzed by 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) afforded the corresponding -trifluoromethyl alcohols in good to excellent yields under mild reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

引用

页码：1523 / 1529

页数：7

共 41 条

[21] A new and efficient method for the trifluoromethylation of carbonyl compounds with trifluoromethyltrimethylsilane in DMSO [J].

Iwanami, K ;

Oriyama, T .

SYNLETT, 2006, (01) :112-114

[22] Copper-Mediated Trifluoromethylation of Heteroaromatic Compounds by Trifluoromethyl Sulfonium Salts [J].

Zhang, Cheng-Pan ;

Wang, Zong-Ling ;

Chen, Qing-Yun ;

Zhang, Chun-Tao ;

Gu, Yu-Cheng ;

Xiao, Ji-Chang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (08) :1896-1900

[23] Quantitative trifluoromethylation of carbonyl-containing lignin model compounds [J].

Ahvazi, BC ;

Argyropoulos, DS .

JOURNAL OF FLUORINE CHEMISTRY, 1996, 78 (02) :195-198

[24] Copper-Catalyzed Trifluoromethylation of Hydrazones Leading to the Formation of Quaternary α-Trifluoromethyl Diazenes [J].

Prieto, Alexis ;

Bouyssi, Didier ;

Monteiro, Nuno .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (06) :742-745

[25] NHC-Catalyzed Electrophilic Trifluoromethylation: Efficient Synthesis of γ-Trifluoromethyl α,β-Unsaturated Esters [J].

Yang, Wen ;

Ma, Dengke ;

Zhou, Yu ;

Dong, Xiuqin ;

Lin, Zhenyang ;

Sun, Jianwei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (37) :12097-12101

[26] TRIFLUOROMETHYLATION AND PENTAFLUOROETHYLATION OF TERPENOID CARBONYL-COMPOUNDS USED IN PERFUMERY [J].

WATANABE, S ;

FUJITA, T ;

SAKAMOTO, M ;

MINO, Y ;

KITAZUME, T .

JOURNAL OF FLUORINE CHEMISTRY, 1995, 73 (01) :21-26

[27] Transition Metal-Catalyzed Trifluoromethylation Reaction of Aromatic Compounds [J].

Qi Zisong ;

Dong Yali ;

Li Yaming ;

Duan Chunying .

PROGRESS IN CHEMISTRY, 2012, 24 (11) :2177-2186

[28] Vanadium-Catalyzed Solvent-Free Synthesis of Quaternary α-Trifluoromethyl Nitriles by Electrophilic Trifluoromethylation [J].

Frueh, Natalja ;

Togni, Antonio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) :10813-10816

[29] Copper-Catalyzed Aerobic Oxidative Trifluoromethylation of H-Phosphonates Using Trimethyl(trifluoromethyl)silane [J].

Chu, Lingling ;

Qing, Feng-Ling .

SYNTHESIS-STUTTGART, 2012, 44 (10) :1521-1525

[30] Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide [J].

Nakamura, Yuzo ;

Fujiu, Motohiro ;

Murase, Tatsuya ;

Itoh, Yoshimitsu ;

Serizawa, Hiroki ;

Aikawa, Kohsuke ;

Mikami, Koichi .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :2404-2409

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