Regioselective synthesis of β-fluoro-α,β-unsaturated ketones by the reaction of β-diketones with DFMBA

被引：18
|
作者：
Sano, Keisuke [1 ]
Fukuhara, Tsuyoshi [1 ]
Hara, Shoji [1 ]
机构：
[1] Hokkaido Univ, Grad Sch Engn, Sapporo, Hokkaido 0608628, Japan
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2009年 / 130卷 / 08期
关键词：
beta-Fluoro-alpha; beta-unsaturated ketone; beta-Diketone; N; N-Diethyl-alpha; alpha-difluoro-m-methylbenzylamine Deoxyfluorination; Regioselective; STEREOSELECTIVE-SYNTHESIS; ALCOHOLS; ENOL; DEOXYFLUORINATION; CARBONYL;
D O I：
10.1016/j.jfluchem.2009.05.009
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The deoxyfluorination reaction of beta-diketones with N,N-diethyl-alpha,alpha-difluoro-m-methylbenzylamine (DFMBA) gave beta-fluoro-alpha,beta-unsaturated ketones in good yields. The reaction proceeded regioselectively, and only one regioisomer was obtained from the unsymmetrical 1-aryl-1,3-diketones. The reaction is applicable to diketones with a trifluoromethyl group, obtaining good yields of 3,4,4,4-tetrafluorobutenones. We used the resulting beta-fluoro-alpha,beta-unsaturated ketones for the reaction with lithium dialkyl cuprates. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码：708 / 713
页数：6
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