Benzyltrifluoromethyl (or Fluoroalkyl) Selenide: Reagent for Electrophilic Trifluoromethyl (or Fluoroalkyl) Selenolation

被引:85
作者
Glenadel, Quentin [1 ]
Ismalaj, Ermal [1 ]
Billard, Thierry [1 ]
机构
[1] Univ Lyon 1, Inst Chem & Biochem ICBMS UMR CNRS 5246, CNRS, 43 Bd 11 Novembre 1918, F-69622 Villeurbanne, France
关键词
FLUORINE; SELENOETHERS; DISULFIDES; KETONES; ARYL; TRIMETHYLSILANE; ALDEHYDES; SULFIDES; IMINES; ACCESS;
D O I
10.1021/acs.joc.6b01344
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trifluoromethylseleno substituent (CF3Se) is an emerging group, but its direct introduction onto organic molecules is still quite limited and mainly restricted to nucleophilic methods. Herein, we describe a new approach to easily and safely perform electrophilic trifluorome-thylselenolation starting from a simple and easily accessible reagent, namely, benzyltrifluoromethyl selenide. This strategy can be generalized to various fluoroalkylselanyl groups, even functionalized ones.
引用
收藏
页码:8268 / 8275
页数:8
相关论文
共 73 条
[1]   Chemical forms of selenium for cancer prevention [J].
Abdulah, R ;
Miyazaki, K ;
Nakazawa, M ;
Koyama, H .
JOURNAL OF TRACE ELEMENTS IN MEDICINE AND BIOLOGY, 2005, 19 (2-3) :141-150
[2]   Selenium and cancer: Some nutritional aspects [J].
Alaejos, MS ;
Romero, FJD ;
Romero, CD .
NUTRITION, 2000, 16 (05) :376-383
[3]   Highly Efficient C-SeCF3 Coupling of Aryl Iodides Enabled by an Air-Stable Dinuclear PdI Catalyst [J].
Aufiero, Marialuisa ;
Sperger, Theresa ;
Tsang, Althea S. -K. ;
Schoenebeck, Franziska .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (35) :10322-10326
[4]  
Becker A., 1996, Inventory of Industrial Fluoro-Biochemicals
[5]   Preparation of trifluoromethyl sulfides or selenides from trifluoromethyl trimethylsilane and thiocyanates or selenocyanates [J].
Billard, T ;
Large, S ;
Langlois, BR .
TETRAHEDRON LETTERS, 1997, 38 (01) :65-68
[6]   Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides [J].
Billard, T ;
Roques, N ;
Langlois, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3813-3820
[7]  
Billard T, 1998, PHOSPHORUS SULFUR, V136, P521
[8]   A new simple access to trifluoromethyl thioethers or selenoethers from trifluoromethyl trimethylsilane and disulfides or diselenides [J].
Billard, T ;
Langlois, BR .
TETRAHEDRON LETTERS, 1996, 37 (38) :6865-6868
[9]   New stable reagents for the nucleophilic trifluoromethylation. Part 4: Trifluoromethylation of disulfides and diselenides with hemiaminals of trifluoroacetaldehyde [J].
Blond, G ;
Billard, T ;
Langlois, BR .
TETRAHEDRON LETTERS, 2001, 42 (13) :2473-2475
[10]   The Properties, Functions, and Use of Selenium Compounds in Living Organisms [J].
Bodnar, Malgorzata ;
Konieczka, Piotr ;
Namiesnik, Jacek .
JOURNAL OF ENVIRONMENTAL SCIENCE AND HEALTH PART C-ENVIRONMENTAL CARCINOGENESIS & ECOTOXICOLOGY REVIEWS, 2012, 30 (03) :225-252