Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones

被引:138
作者
Prakash, GKS [1 ]
Hu, JB
Olah, GA
机构
[1] Univ So Calif, Donald P & Katherine B Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA
[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA
关键词
D O I
10.1021/jo030110z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient method for the preparation of tri- and difluoromethylsilanes using magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes is reported using tri- and difluoromethyl sulfides, sulfoxides, and sulfones. The byproduct of the process is diphenyl disulfide. Since phenyl trifluoromethyl sulfone, sulfoxide, and sulfide are readily prepared from trifluoromethane (CF3H) and diphenyl disulfide, the method can be considered to be catalytic in diphenyl disulfide for the preparation of (trifluoromethyl)trimethylsilane (TMS-CF3) from non-ozone-depleting trifluoromethane.
引用
收藏
页码:4457 / 4463
页数:7
相关论文
共 49 条
[1]   Nucleophilic trifluoromethylation using trifluoromethyl iodide.: A new and simple alternative for the trifluoromethylation of aldehydes and ketones [J].
Aït-Mohand, S ;
Takechi, N ;
Médebielle, M ;
Dolbier, WR .
ORGANIC LETTERS, 2001, 3 (26) :4271-4273
[2]   Mg0-promoted selective C-F bond cleavage of trifluoromethyl ketones:: a convenient method for the synthesis of 2,2-difluoro enol silanes [J].
Amii, H ;
Kobayashi, T ;
Hatamoto, Y ;
Uneyama, K .
CHEMICAL COMMUNICATIONS, 1999, (14) :1323-1324
[3]   New C-F bond-cleavage route for the synthesis of octafluoro[2.2]paracyclophane [J].
Amii, H ;
Hatamoto, Y ;
Seo, M ;
Uneyama, K .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :7216-7218
[4]  
Amii H, 2000, SYNTHESIS-STUTTGART, P2001
[5]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[6]   AN EFFICIENT INEXPENSIVE ELECTROCHEMICAL PREPARATION OF RUPPERTS REAGENT [J].
AYMARD, F ;
NEDELEC, JY ;
PERICHON, J .
TETRAHEDRON LETTERS, 1994, 35 (46) :8623-8624
[7]  
Banks R.E., 1994, ORGANOFLUORINE CHEM
[8]   New stable reagents for the nucleophilic trifluoromethylation.: 1.: Trifluoromethylation of carbonyl compounds with N-formylmorpholine derivatives [J].
Billard, T ;
Bruns, S ;
Langlois, BR .
ORGANIC LETTERS, 2000, 2 (14) :2101-2103
[9]  
Billard T, 2001, EUR J ORG CHEM, V2001, P1467
[10]   A SIMPLE, HIGH-YIELD SYNTHESIS OF TRIFLUOROPYRUVIC ACID MONOHYDRATE [J].
BROICHER, V ;
GEFFKEN, D .
TETRAHEDRON LETTERS, 1989, 30 (39) :5243-5244