Download PDF
Synthesis 2004(17): 2821-2824  
DOI: 10.1055/s-2004-834857
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Efficient Stereoselective Synthesis of (E)-β-Fluoroalkenyliodonium Salts

Masanori Yoshida*, Keiji Kawakami, Shoji Hara*
Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
Fax: +81(11)7066557; e-Mail: myoshida@org-mc.eng.hokudai.ac.jp;
Further Information

Publication History

Received 24 June 2004
Publication Date:
07 October 2004 (online)

   Buy Article Permissions and Reprints All articles of this category
Zoom Image

Abstract

Stereoselective synthesis of (E)-β-fluoroalkenyliodonium salts was performed by the treatment of alk-1-ynes with p-iodo­toluene difluoride in the presence of HBF4-Et2O. The reaction occurred instantaneously at -78 °C to give the fluoroalkenyliodonium salts in good yields with high stereoselectivity. The Pd-catalyzed carbomethoxylation of the fluoroalkenyliodonium salt was also carried out to obtain a (E)-β-fluoro-α,β-unsaturated ester.

Key words

iodonium salt - fluoroalkene - p-iodotoluene difluoride - stereoselective synthesis - fluorination reaction