使用由（2-氟-1-烯基）碘鎓盐生成的2-氟亚烷基碘叶立德对（E）-和（Z）-氟代烯基硼酸酯进行立体选择性合成。

Stereoselective synthesis of (E)- and (Z)-Fluoroalkenylboronates using 2-fluoroalkylideneiodonium ylides generated from (2-fluoro-1-alkenyl)iodonium salts.

作者信息

Guan Tong, Yoshida Masanori, Hara Shoji

机构信息

Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.

出版信息

J Org Chem. 2007 Dec 7;72(25):9617-21. doi: 10.1021/jo701784t. Epub 2007 Nov 3.

DOI:10.1021/jo701784t

PMID:17979292

Abstract

(E)- and (Z)-(fluoroalkenyl)boronates were prepared stereospecifically by the reaction of 2-fluoroalkylideneiodonium ylide generated from (E)- or (Z)-(2-fluoroalkenyl)iodonium salts with di(p-fluorophenoxy)alkylboranes, followed by transesterification to pinacol esters. The resulting pinacol esters of (fluoroalkenyl)boranes were used for the stereoselective synthesis of trisubstituted fluoroalkenes by cross-coupling reactions.

摘要

通过（E）-或（Z）-（2-氟代烯基）碘鎓盐生成的2-氟代亚烷基碘鎓叶立德与二（对氟苯氧基）烷基硼烷反应，立体定向地制备了（E）-和（Z）-（氟代烯基）硼酸酯，随后酯交换为频哪醇酯。所得的（氟代烯基）硼烷频哪醇酯用于通过交叉偶联反应立体选择性合成三取代氟代烯烃。