Preparation and Addition-Elimination Reactions of Benzyl ,
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- 作者：Shigeyuki Yamada ; Mayumi Noma ; Kazunori Hondo ; Tsutomu Konno ; Takashi Ishihara
- 刊名：Journal of Organic Chemistry
- 出版年：2008
- 出版时间：January 18, 2008
- 年：2008
- 卷：73
- 期：2
- 页码：522 - 528
- 全文大小：129K
- 年卷期：v.73,no.2(January 18, 2008)
- ISSN：1520-6904
文摘
gifchars/alpha.gif" BORDER=0>,gifchars/beta2.gif" BORDER=0 ALIGN="middle">,gifchars/beta2.gif" BORDER=0 ALIGN="middle">-trifluoroacrylate (1) was prepared in good yield via the reductive Br-F elimination ofbenzyl 2-bromo-2,3,3,3-tetrafluoropropanoate or the palladium-catalyzed cross-coupling reaction of 1,2,2-trifluorovinylstannane with benzyl chloroformate. On treating 1 with various Grignard reagents ordialkylzinc reagents in the presence of copper(I) salt, the corresponding gifchars/beta2.gif" BORDER=0 ALIGN="middle">-substituted gifchars/alpha.gif" BORDER=0>,gifchars/beta2.gif" BORDER=0 ALIGN="middle">-difluoroacrylateswere obtained in high yields with high Z-selectivity. Additionally, trialkylaluminum reagents were alsofound to be good nucleophiles, the corresponding addition-elimination products being afforded in goodyields but with low stereoselectivity.