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

[31] Palladium-Catalyzed Selective Reduction of Carbonyl Compounds [J].

Sarkar, Nabin ;

Mahato, Mamata ;

Nembenna, Sharanappa .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (23) :2295-2301

[32] Copper-Catalyzed One-Pot Trifluoromethylation/Aryl Migration/Carbonyl Formation with Homopropargylic Alcohols [J].

Gao, Pin ;

Shen, Yong-Wen ;

Fang, Ran ;

Hao, Xin-Hua ;

Qiu, Zi-Hang ;

Yang, Fan ;

Yan, Xiao-Biao ;

Wang, Qiang ;

Gong, Xiang-Jun ;

Liu, Xue-Yuan ;

Liang, Yong-Min .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (29) :7629-7633

[33] Radical C-H Bond Trifluoromethylation of Alkenes by High-Valent Copper(III) Trifluoromethyl Compounds [J].

Zhang, Hao-Ran ;

Xiao, Chang ;

Zhang, Song-Lin ;

Zhang, Xiaoming .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (23) :5305-5310

[34] Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals [J].

Ito, Suguru ;

Hayashi, Akira ;

Komai, Hirotomo ;

Yamaguchi, Hitoshi ;

Kubota, Yoshihiro ;

Asami, Masatoshi .

TETRAHEDRON, 2011, 67 (11) :2081-2089

[35] Trifluoromethylation-Initiated Remote Cross-Coupling of Carbonyl Compounds to Form Carbon-Heteroatom/Carbon Bonds [J].

Huang, Lin ;

Zheng, Sheng-Cai ;

Tan, Bin ;

Liu, Xin-Yuan .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (18) :6718-6722

[36] Stereoselective Synthesis of α-Trifluoromethyl Enones by AuI/CuI-Co-Catalyzed Tandem 1,3-Acyloxy Migration/Trifluoromethylation Reaction of Propargyl Acetates [J].

Ji, Yun-Long ;

Lin, Jin-Hong ;

Xiao, Ji-Chang ;

Gu, Yu-Cheng .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (35) :7948-7954

[37] Copper-Catalyzed Trifluoromethylation of Acrylamides Coupled with Indole Dearomatization: Access to Trifluoromethyl-Substituted Spiro[indole-3,3′-pyrrolidine] Derivatives [J].

Han, Guifang ;

Wang, Qiang ;

Chen, Linwei ;

Liu, Yuxiu ;

Wang, Qingmin .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (04) :561-566

[38] Syntheses of 2-(trifluoromethyl)-1,3-dicarbonyl compounds through direct trifluoromethylation with CF3I and their application to fluorinated pyrazoles syntheses [J].

Ohtsuka, Yuhki ;

Uraguchi, Daisuke ;

Yamamoto, Kyoko ;

Tokuhisa, Kenji ;

Yamakawa, Tetsu .

TETRAHEDRON, 2012, 68 (12) :2636-2649

[39] Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds [J].

Dong, Xiang ;

Sang, Rui ;

Wang, Qiang ;

Tang, Xiang-Ying ;

Shi, Min .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (50) :16910-16915

[40] Copper-catalyzed remote oxidation of alcohols initiated by radical difluoroalkylation of alkenes: facile access to difluoroalkylated carbonyl compounds [J].

Zhang, Jian ;

Jin, Weiwei ;

Cheng, Cungui ;

Luo, Fang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (21) :3876-3880

← 1 2 3 4 5 →