Trifluoromethylation of Carbonyl Compounds

被引：19

作者：

Boechat, N. ^{[1
]}

Bastos, M. M. ^{[1
]}

机构：

[1] Fundacao Oswaldo Cruz, BR-21041250 Rio De Janeiro, Brazil

来源：

CURRENT ORGANIC SYNTHESIS | 2010年 / 7卷 / 05期

关键词：

Carbonyl compounds; nucleophilic reagents; sulfur tetrafluoride; TDAE; trifluoromethylation; trifluoromethyltrimethylsilane; NUCLEOPHILIC TRIFLUOROMETHYLATION; ENANTIOSELECTIVE TRIFLUOROMETHYLATION; CATALYZED TRIFLUOROMETHYLATION; ELECTROORGANIC CHEMISTRY; STABLE REAGENTS; ALDEHYDES; KETONES; TRIFLUOROMETHYLTRIMETHYLSILANE; PERFLUOROALKYLATION; BASE;

D O I：

10.2174/157017910792246081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper reviews the recent findings on trifluoromethylation of carbonyl compounds. Emphasis was given to the description of the trifluoromethylating agents, their activation mode, their reaction with carbonyl compounds, as well as applications in organic synthesis.

引用

页码：403 / 413

页数：11

共 88 条

[41] NEW FLUORINATING REAGENTS - DIALKYLAMINOSULFUR FLUORIDES [J].

MIDDLETON, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05) :574-578

[42] Tri-tert-butylphosphine is an efficient promoter for the trifluoromethylation reactions of aldehydes, ketones, imides and imines [J].

Mizuta, S ;

Shibata, N ;

Sato, T ;

Fujimoto, H ;

Nakamura, S ;

Toru, T .

SYNLETT, 2006, (02) :267-270

[43] Ammonium bromides/KF catalyzed trifluoromethylation of carbonyl compounds with (trifluoromethyl) trimethylsilane and its application in the enantioselective trifluoromethylation reaction [J].

Mizuta, Satoshi ;

Shibata, Norio ;

Hibino, Motoki ;

Nagano, Shinichi ;

Nakamura, Shuichi ;

Toru, Takeshi .

TETRAHEDRON, 2007, 63 (35) :8521-8528

[44] Cinchona Alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones [J].

Mizuta, Satoshi ;

Shibata, Norio ;

Akiti, Surendar ;

Fujimoto, Hiroyuki ;

Nakamura, Shuichi ;

Toru, Takeshi .

ORGANIC LETTERS, 2007, 9 (18) :3707-3710

[45] Lithium acetate-catalyzed trifluoromethylation of carbonyl compounds with (trifluoromethyl)trimethylsilane [J].

Mukaiyama, T ;

Kawano, Y ;

Fujisawa, H .

CHEMISTRY LETTERS, 2005, 34 (01) :88-89

[46] Enantioselective trifluoromethylation of ketones with (trifluoromethyl)trimethylsilane catalyzed by chiral quaternary ammonium phenoxides [J].

Nagao, Hitoshi ;

Kawano, Yoshikazu ;

Mukaiyama, Teruaki .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2007, 80 (12) :2406-2412

[47] Enantiopure quaternary α-trifluoromethyl-α-alkoxyaldehydes from L-tartaric acid derived ketoamides [J].

Nonnenmacher, Jean ;

Massicot, Fabien ;

Grellepois, Fabienne ;

Portella, Charles .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) :7990-7995

[48]

Ojima I., 2009, Fluorine In Medicinal Chemistry and Chemical Biology

[49] PALLADIUM AND NICKEL-CATALYZED PERFLUOROALKYLATION OF ALDEHYDES USING ZINC AND PERFLUOROALKYL HALIDES [J].

OREILLY, NJ ;

MARUTA, M ;

ISHIKAWA, N .

CHEMISTRY LETTERS, 1984, (04) :517-520

[50] Use of Lawesson's reagent in organic syntheses [J].

Ozturk, Turan ;

Ertas, Erdal ;

Mert, Olcay .

CHEMICAL REVIEWS, 2007, 107 (11) :5210-5278

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