Organocatalytic direct difluoromethylation of aldehydes and ketones with TMSCF2H

被引：33

作者：

Du, Guang-Fen ^{[1
,2
]}

Wang, Ying ^{[1
]}

Gu, Cheng-Zhi ^{[1
]}

Dai, Bin ^{[1
]}

He, Lin ^{[1
]}

机构：

[1] Shihezi Univ, Sch Chem & Chem Engn, Xinjiang Uygur 832000, Peoples R China

[2] Tianjin Univ, Sch Chem Engn & Technol, Tianjin 300072, Peoples R China

来源：

RSC ADVANCES | 2015年 / 5卷 / 45期

基金：

中国国家自然科学基金;

关键词：

LEWIS-BASE CATALYST; CARBONYL-COMPOUNDS; NUCLEOPHILIC DIFLUOROMETHYLATION; DEPROTONATIVE FUNCTIONALIZATION; STEREOSELECTIVE-SYNTHESIS; ORGANOZINC REAGENTS; S(N)2' REACTION; ALKYL-HALIDES; T-BU-P4; BASE; TRIFLUOROMETHYLATION;

D O I：

10.1039/c5ra04472c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An organic Lewis base promoted direct difluoromethylation reaction of carbonyl compounds with Me3SiCF2H has been studied. The Schwesinger's superbase can efficiently activate the Si-CF2H bond and initiate the difluoromethylation of aldehydes and ketones under very mild conditions, producing difluoromethyl adducts in 42-99% yields.

引用

页码：35421 / 35424

页数：4

共 73 条

[1] Functionalisation of heteroaromatic N-oxides using organic superbase catalyst [J].

Araki, Yuta ;

Kobayashi, Koji ;

Yonemoto, Misato ;

Kondo, Yoshinori .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (01) :78-80

[2] Recent Progress in Direct Introduction of Fluorinated Groups on Alkenes and Alkynes by means of C-H Bond Functionalization [J].

Besset, Tatiana ;

Poisson, Thomas ;

Pannecoucke, Xavier .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) :16830-16845

[3] Tamed Arene and Heteroarene Trifluoromethylation [J].

Besset, Tatiana ;

Schneider, Cedric ;

Cahard, Dominique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050

[4]

Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine

[5] Fluoride-Catalyzed Addition of PhSCF2SiMe3 to N-Substituted Cyclic Imides Followed by Radical Cyclization: General Synthetic Strategy of gem-Difluoromethylenated 1-Azabicyclic Compounds [J].

Bootwicha, Teerawut ;

Panichakul, Duanghathai ;

Kuhakarn, Chutima ;

Prabpai, Samran ;

Kongsaeree, Palangpon ;

Tuchinda, Patoomratana ;

Reutrakul, Vichai ;

Pohmakotr, Manat .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :3798-3805

[6] A FACILE, GENERAL-ROUTE TO PERFLUOROALKYL ALLENES [J].

BURTON, DJ ;

HARTGRAVES, GA ;

HSU, J .

TETRAHEDRON LETTERS, 1990, 31 (26) :3699-3702

[7] The preparation of HCF2CdX and HCF2ZnX via direct insertion into the carbon halogen bond of CF2HY (Y = Br, I) [J].

Burton, Donald J. ;

Hartgraves, Greg A. .

JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (10) :1198-1215

[8] P(PhCH2NCH2CH2)3N Catalysis of Mukaiyama Aldol Reactions of Aliphatic, Aromatic, and Heterocyclic Aldehydes and Trifluoromethyl Phenyl Ketone [J].

Chintareddy, Venkat Reddy ;

Wadhwa, Kuldeep ;

Verkade, John G. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8118-8132

[9] Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source [J].

Chu, Lingling ;

Qing, Feng-Ling .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1513-1522

[10] Bu4N+ Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes [J].

Das, Manas ;

O'Shea, Donal F. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12) :5595-5607

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