REACTIONS OF 1,1-DIHALOALKENES WITH TRIORGANOZINCATES - A NOVEL METHOD FOR THE PREPARATION OF ALKENYLZINC SPECIES ASSOCIATED WITH CARBON-CARBON BOND FORMATION

被引：95
作者：
HARADA, T
KATSUHIRA, T
HARA, D
KOTANI, Y
MAEJIMA, K
KAJI, R
OKU, A
机构：
[1] Department of Chemistry, Kyoto Institute of Technology, Kyoto 606, Matsugasaki, Sakyo-ku
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 18期
关键词：
D O I：
10.1021/jo00070a027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lithium trialkylzincates react with 1,1-dibromoalkenes 1 and 1-bromo-1-chloroalkenes 2 at -85-degrees-C in THF to give 1-bromoalkenes 5 and 1-chloroalkenes 7, respectively, upon hydrolysis. The intermediate (1-haloalkenyl)zincates 4 and 6 are stable at low temperature but, when allowed to warm to 0-degrees-C, they undergo a 1,2-alkyl migration reaction to afford alkenylzinc species 10. A variety of alkylation products 11 are obtained by the hydrolysis of 10. In the presence of (Ph3P)2Pd (5 mol%), alkenylzinc species 10 react smoothly with organic halides (AcCl, EtOCOCl, CH2=CH-(Me)Br, PhBr) to yield the corresponding coupling products 13-16.
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页码：4897 / 4907
页数：11
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