A Convergent, Unified Approach to Functionalized Fluoro- and Trifluoromethyl Alkenes

被引：31
作者：
Debien, Laurent [1 ]
Quiclet-Sire, Beatrice [1 ]
Zard, Samir S. [1 ]
机构：
[1] Ecole Polytech, CNRS, Synth Organ Lab, UMR 7652, F-91128 Palaiseau, France
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 19期
关键词：
PALLADIUM-CATALYZED TRIFLUOROMETHYLATION; CARBOXYLIC-ACIDS; ALLYLIC ALCOHOLS; KETONES; ELIMINATION; ALDEHYDES; ACCESS; ARENES; COPPER; ROUTE;
D O I：
10.1021/ol3023903
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A modular, convergent, and operationally simple route to trifluoromethyl alkenes and vinyl fluorides involving a unique carbon-oxygen bond homolysis is reported. Highly functionalized trifluoromethyl alkenes and vinyl fluorides were obtained in good yields and good selectivity.
引用
收藏
页码：5118 / 5121
页数：4
相关论文
共 64 条
[1]   FLUORINE-CONTAINING ORGANOZINC REAGENTS .6. THE PREPARATION OF ALPHA-TRIFLUOROMETHYL-ALPHA-BETA-UNSATURATED CARBOXYLIC-ACID ESTERS [J].
ALLMENDINGER, T ;
LANG, RW .
TETRAHEDRON LETTERS, 1991, 32 (03) :339-340
[2]   Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].
Ball, Nicholas D. ;
Kampf, Jeff W. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+
[3]   S-(3-Chloro-2-oxo-propyl)-O-ethyl xanthate:: a linchpin radical coupling agent for the synthesis of heterocyclic and polycyclic compounds [J].
Bergeot, O ;
Corsi, C ;
El Qacemi, M ;
Zard, SZ .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (02) :278-290
[4]   TRIFLUOROMETHYL KETONES FROM CARBOXYLIC-ACIDS .2. A VERSATILE ACCESS TO TRIFLUOROMETHYLATED HETEROCYCLES [J].
BOIVIN, J ;
ELKAIM, L ;
ZARD, SZ .
TETRAHEDRON, 1995, 51 (09) :2585-2592
[5]   AN EXPEDIENT ACCESS TO TRIFLUOROMETHYL KETONES FROM CARBOXYLIC-ACIDS [J].
BOIVIN, J ;
ELKAIM, L ;
ZARD, SZ .
TETRAHEDRON LETTERS, 1992, 33 (10) :1285-1288
[6]   A NEW AND EFFICIENT SYNTHESIS OF TRIFLUOROMETHYL KETONES FROM CARBOXYLIC-ACIDS .1. [J].
BOIVIN, J ;
ELKAIM, L ;
ZARD, SZ .
TETRAHEDRON, 1995, 51 (09) :2573-2584
[7]   A Highly Stereoselective, Modular Route to (E)-Vinylsulfones and to (Z)- and (E)-Alkenes [J].
Braun, Marie-Gabrielle ;
Quiclet-Sire, Beatrice ;
Zard, Samir Z. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (40) :15954-15957
[8]   Elimination versus Ring Opening: A Convergent Route to Allrylidene-Cyclobutanes [J].
Brioche, Julien ;
Michalak, Michal ;
Quiclet-Sire, Beatrice ;
Zard, Samir Z. .
ORGANIC LETTERS, 2011, 13 (23) :6296-6299
[9]   Allylic alcohols as radical allylating agents. An overall olefination of aldehydes and ketones [J].
Charrier, Nicolas ;
Quiclet-Sire, Beatrice ;
Zard, Samir Z. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8898-+
[10]   STRUCTURAL AND CHEMICAL-PROPERTIES OF SILYL RADICALS [J].
CHATGILIALOGLU, C .
CHEMICAL REVIEWS, 1995, 95 (05) :1229-1251
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