Hydrotrifluoromethylthiolation of α-diazo esters - synthesis of α-SCF3 substituted esters

被引:105
作者
Lefebvre, Quentin [1 ]
Fava, Eleonora [1 ]
Nikolaienko, Pavlo [1 ]
Rueping, Magnus [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
NUCLEOPHILIC TRIFLUOROMETHYLTHIOLATION; 3-COMPONENT REACTION; CATALYZED SYNTHESIS; NATURAL-PRODUCTS; DIAZOACETATES; INSERTION; FLUORINE; REACTIVITY; REAGENTS; ALCOHOLS;
D O I
10.1039/c4cc02060j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A practical protocol for hydrotrifluoromethylthiolation of diazo compounds has been developed. A range of diazo compounds in combination with a nucleophilic SCF3 source provided access to valuable trifluoromethylthiolated compounds. Furthermore, a methodology for the first double trifluoromethylthiolation was developed.
引用
收藏
页码:6617 / 6619
页数:3
相关论文
共 55 条
[1]   Trifluoromethylthiodediazoniation: a simple, efficient route to trifluoromethyl aryl sulfides [J].
Adams, DJ ;
Goddard, A ;
Clark, JH ;
Macquarrie, DJ .
CHEMICAL COMMUNICATIONS, 2000, (11) :987-988
[2]   Base-Catalyzed Electrophilic Trifluoromethylthiolation of Terminal Alkynes [J].
Alazet, Sebastien ;
Zimmer, Luc ;
Billard, Thierry .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (41) :10814-10817
[3]   Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen- or sulfur-containing nucleophilic substrates: Synthetic uses and mechanistic insights [J].
Aviv, Iris ;
Gross, Zeev .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (13) :3995-4005
[4]   Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides [J].
Baert, Francois ;
Colomb, Julie ;
Billard, Thierry .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10382-10385
[5]   Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation [J].
Boiko, Vladimir N. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6 :880-921
[6]   N-Trifluoromethylthiophthalimide: A Stable Electrophilic SCF3-Reagent and its Application in the Catalytic Asymmetric Trifluoromethylsulfenylation [J].
Bootwicha, Teerawut ;
Liu, Xiangqian ;
Pluta, Roman ;
Atodiresei, Iuliana ;
Rueping, Magnus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) :12856-12859
[7]   Diazo Reagents with Small Steric Footprints for Simultaneous Arming/SAR Studies of Alcohol-Containing Natural Products via O-H Insertion [J].
Chamni, Supakarn ;
He, Qing-Li ;
Dang, Yongjun ;
Bhat, Shridhar ;
Liu, Jun O. ;
Romo, Daniel .
ACS CHEMICAL BIOLOGY, 2011, 6 (11) :1175-1181
[8]  
Chen P., 2013, SYNTHESIS-STUTTGART, P2919
[9]   DIRECT TRIFLUOROMETHYLTHIOLATION OF ARYL HALIDES USING METHYL FLUOROSULFONYLDIFLUOROACETATE AND SULFUR [J].
CHEN, QY ;
DUAN, JX .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (11) :918-919
[10]   THE INTRODUCTION OF SCF3 INTO AROMATIC SUBSTRATES USING CUSCF3 AND ALUMINA-SUPPORTED CUSCF3 [J].
CLARK, JH ;
JONES, CW ;
KYBETT, AP ;
MCCLINTON, MA ;
MILLER, JM ;
BISHOP, D ;
BLADE, RJ .
JOURNAL OF FLUORINE CHEMISTRY, 1990, 48 (02) :249-255