Photoredox Catalysis: A Mild, Operationally Simple Approach to the Synthesis of α-Trifluoromethyl Carbonyl Compounds

被引：410

作者：

Pham, Phong V. ^{[1
]}

Nagib, David A. ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 27期

关键词：

enolsilanes; photoredox catalysis; alpha-perfluoroalkylation; alpha-trifluoromethylation; SILYL ENOL ETHERS; VISIBLE-LIGHT PHOTOCATALYSIS; PHOTOINDUCED-ELECTRON-TRANSFER; C-H FUNCTIONALIZATION; ELECTROCHEMICAL OXIDATION; MEDICINAL CHEMISTRY; CATION-RADICALS; KETENE ACETALS; ALDEHYDES; ORGANOCATALYSIS;

D O I：

10.1002/anie.201101861

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and efficient method for the α-trifluoromethylation of carbonyl compounds and enolsilanes has been accomplished through application of a photoredox catalysis strategy. A one-flask procedure for the direct α-trifluoromethylation and α-perfluoroalkylation of ketone, amide, and ester substrates as well as silylketene acetals is described (see scheme). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6119 / 6122

页数：4

共 57 条

[1] The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].

Allen, Anna E. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+

[2] PHOTOCHEMICAL GENERATION OF RU(BPY)3+ AND O2- [J].

ANDERSON, CP ;

SALMON, DJ ;

MEYER, TJ ;

YOUNG, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) :1980-1982

[3] Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].

Andrews, R. Stephen ;

Becker, Jennifer J. ;

Gagne, Michel R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276

[4]

Andrews S. R., 2010, ANGEW CHEM, V122, P7432

[5] Electrochemical oxidation of some enol silyl ethers; investigations on the reactivity of cyclizable cation-radicals [J].

Audebert, P ;

Roche, M ;

Bekolo, H .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1998, 445 (1-2) :203-209

[6]

Banks R.E., 1994, Organofluorine Chemistry: Principles and Commercial Applications, P237

[7] Synthesis, characterization and biological evaluation of 7α-perfluoroalkylestradiol derivatives [J].

Blazejewski, JC ;

Wilmshurst, MP ;

Popkin, MD ;

Wakselman, C ;

Laurent, G ;

Nonclercq, D ;

Cleeren, A ;

Ma, Y ;

Seo, HS ;

Leclercq, G .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (03) :335-345

[8]

CANTACUZENE D, 1975, TETRAHEDRON LETT, P2031

[9] EXPERIMENTAL INVESTIGATION OF EXCITED-STATE ELECTRON-TRANSFER REACTION - EFFECTS OF FREE-ENERGY AND SOLVENT ON RATES [J].

CHEN, JM ;

HO, TI ;

MOU, CY .

JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (07) :2889-2896

[10] Photoaddition reactions of 1,2-diketones with silyl ketene acetals.: Formation of β-hydroxy-γ-ketoesters [J].

Cho, Dae Won ;

Lee, Hyang-Yeol ;

Oh, Sun Wha ;

Choi, Jung Hei ;

Park, Hea Jung ;

Mariano, Patrick S. ;

Yoon, Ung Chan .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4539-4547

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