Difluorohomologation of Ketones

被引：67

作者：

Kosobokov, Mikhail D. ^{[1
]}

Levin, Vitalij V. ^{[1
]}

Struchkova, Marina I. ^{[1
]}

Dilman, Alexander D. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 03期

基金：

俄罗斯基础研究基金会;

关键词：

FREE CLICK CHEMISTRY; ORGANOZINC REAGENTS; ALPHA-ARYLATION; ARYL BROMIDES; CF2; GROUP; ALPHA; ALPHA-DIFLUOROKETONES; DIFLUOROCARBENE; ROUTE; ACIDS; DIFLUORINATION;

D O I：

10.1021/acs.orglett.5b00097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the homologation of ketones with the CF2 fragment is described. The reaction involves silylation, room-temperature difluorocyclopropanation of silyl enol ethers, and selective ring opening of cyclopropanes under acidic conditions. The whole three-step sequence is conveniently performed in a one-pot mode.

引用

页码：760 / 763

页数：4

共 49 条

[1]

[Anonymous], 2008, BIOORGAN MED CHEM

[2] Copper-free click chemistry for dynamic in vivo imaging [J].

Baskin, Jeremy M. ;

Prescher, Jennifer A. ;

Laughlin, Scott T. ;

Agard, Nicholas J. ;

Chang, Pamela V. ;

Miller, Isaac A. ;

Lo, Anderson ;

Codelli, Julian A. ;

Bertozzi, Carolyn R. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797

[3] New methodology for the synthesis of α,α-difluoroketones [J].

Biju, Purakkattle .

SYNTHETIC COMMUNICATIONS, 2008, 38 (12) :1940-1945

[4] MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID [J].

BLACKBURN, GM ;

ENGLAND, DA ;

KOLKMANN, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) :930-932

[5] Second-generation difluorinated cyclooctynes for copper-free click chemistry [J].

Codelli, Julian A. ;

Baskin, Jeremy M. ;

Agard, Nicholas J. ;

Berozzi, Carolyn R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11486-11493

[6] CHEMISTRY OF DIFLUOROCYCLOPROPYL ACETATES - APPLICATION OF DIFLUOROCARBENE CHEMISTRY TO HOMOLOGATION REACTIONS [J].

CRABBE, P ;

CERVANTE.A ;

CRUZ, A ;

GALEAZZI, E ;

IRIARTE, J ;

VELARDE, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (20) :6655-6665

[7] SELECTIVE MONOFLUORINATION AND DIFLUORINATION OF ENOLATES [J].

DIFFERDING, E ;

RUEGG, GM ;

LANG, RW .

TETRAHEDRON LETTERS, 1991, 32 (15) :1779-1782

[8] Structure, synthesis, and chemical reactions of fluorinated cyclopropanes and cyclopropenes [J].

Dolbier, WR ;

Battiste, MA .

CHEMICAL REVIEWS, 2003, 103 (04) :1071-1098

[9]

EMDE H, 1982, SYNTHESIS-STUTTGART, P1

[10] Pd-Catalyzed α-Arylation of α,α-Difluoroketones with Aryl Bromides and Chlorides. A Route to Difluoromethylarenes [J].

Ge, Shaozhong ;

Chaladaj, Wojciech ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (11) :4149-4152

← 1 2 3 4 5 →