A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation

被引：34

作者：

Tanaka, Yusuke ^{[1
]}

Ishihara, Takashi ^{[1
]}

Konno, Tsutomu ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6060962, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2012年 / 137卷

关键词：

Fluoroalkyl-substituted methanols; Sodium; 2-iodobenzenesulfonate; Oxone (R); Hypervalent iodine(V); TRIFLUOROACETALDEHYDE ETHYL HEMIACETAL; ALPHA-KETO ESTERS; TRIFLUOROMETHYL KETONES; 2-IODOXYBENZENESULFONIC ACID; MEDICINAL CHEMISTRY; EFFICIENT SYNTHESIS; ALDEHYDES; FLUORINE; ALCOHOLS; PERFLUOROALKYLATION;

D O I：

10.1016/j.jfluchem.2012.03.002

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Oxidation of various fluoroalkyl-substituted methanol derivatives under the influence of a catalytic amount of sodium 2-iodobenzenesulfonate and Oxone (R) in CH3CN or CH3NO2 was investigated in detail. The efficiency of the newly developed oxidation was also evaluated by comparison to other oxidations, such as Dess-Martin, PDC, and Swern oxidation. (c) 2012 Elsevier B.V. All rights reserved.

引用

页码：99 / 104

页数：6

共 58 条

[1] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products [J].

Begue, Jean-Pierre ;

Bonnet-Delpon, Daniele .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :992-1012

[2] PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES [J].

BEGUE, JP ;

BONNETDELPON, D .

TETRAHEDRON, 1991, 47 (20-21) :3207-3258

[3] Catalytic asymmetric fluorinations [J].

Bobbio, Carla ;

Gouverneur, Veronique .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2065-2075

[4] REACTION OF ORGANOMETALLIC REAGENTS WITH ETHYL TRIFLUOROACETATE AND DIETHYL OXALATE - FORMATION OF TRIFLUOROMETHYL KETONES AND ALPHA-KETO ESTERS VIA STABLE TETRAHEDRAL ADDUCTS [J].

CREARY, X .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :5026-5030

[5] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[6] ALPHA,BETA-DIPHENYL-ALPHA-TRIFLUOROMETHYL-2-PYRIDINEETHANOL AND RELATED COMPOUNDS AS SYNTHETIC ESTROGENS [J].

DICE, JR ;

SCHEINMAN, L ;

BERRODIN, KW .

JOURNAL OF MEDICINAL CHEMISTRY, 1966, 9 (02) :176-+

[7]

Fäh C, 2010, EUR J ORG CHEM, V2010, P4617, DOI [10.1002/ejoc.201000712, 10.1002/ejoe.201000712]

[8] New organofluorine building blocks: inhibition of the malarial aspartic proteases plasmepsin II and IV by alicyclic α,α-difluoroketone hydrates [J].

Faeh, Christoph ;

Hardegger, Leo A. ;

Baitsch, Lukas ;

Schweizer, W. Bernd ;

Meyer, Solange ;

Bur, Daniel ;

Diederich, Francois .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (19) :3947-3957

[9] The use of trifluoroacetaldehyde ethyl hemiacetal or hydrate in a simple and practical regioselective synthesis of β-hydroxy-β-trifluoromethyl ketones from enamines and imines [J].

Funabiki, K ;

Matsunaga, K ;

Nojiri, M ;

Hashimoto, W ;

Yamamoto, H ;

Shibata, K ;

Matsui, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2853-2860

[10] NUCLEOPHILIC-ADDITION OF THE PENTAFLUOROETHYL GROUP TO ALDEHYDES, KETONES, AND ESTERS [J].

GASSMAN, PG ;

OREILLY, NJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2481-2490

← 1 2 3 4 5 6 →