Selective electrochemical synthesis and reactivity of functional benzylic fluorosilylsynthons

被引：52
|
作者：
Clavel, P
Lessene, G
Biran, C
Bordeau, M
Roques, N
Trévin, S
de Montauzon, D
机构：
[1] Univ Bordeaux 1, LCOO, F-33405 Talence, France
[2] Rhodia Rech, F-69192 St Fons, France
[3] Elect France, DER Renardieres, F-77818 Moret Sur Loing, France
[4] Univ Toulouse 3, UPR 8241, LCC, F-31077 Toulouse, France
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2001年 / 107卷 / 02期
关键词：
fluoro-benzylsilanes; electrosynthesis; sacrificial aluminium anode; cyclic voltammetry; solvent effect; difluorobenzylation;
D O I：
10.1016/S0022-1139(00)00373-0
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Electrochemical reductive silylation of meta-(trifluoromethyl)arenes by the sacrificial anode technique selectively led to meta-trimethylsilyldifluoromethylarenes (ArCF2TMS), in the presence of an excess of TMSCl and in a THF/cosolvent mixture (cosolvent = DMPU or HMPA). In the case of meta-(trimethylsilyldifluoromethyl)trifluoromethylbenzene, the influence of the cosolvent on the silylation selectivity was studied. A cyclic voltammetry study allowed an explanation of the difference in the results obtained between the trifluoromethylbenzene and meta-bistrifluoromethylbenzene series. ArCF2TMS (Ar = Ph, m-CF3C6H4) species were found efficient for ArCF2-group transfer to diverse electrophiles under Fuchigami's conditions (KF catalysis in DMF). (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码：301 / 310
页数：10
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