Synthesis 2015; 47(18): 2839-2843
DOI: 10.1055/s-0034-1381003
paper
© Georg Thieme Verlag Stuttgart · New York

Iodofluorination of Alkenes Using IF5–Pyridine–HF

Shohei Yano
Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan   Email: shara@eng.hokudai.ac.jp
,
Shoji Hara*
Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan   Email: shara@eng.hokudai.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 25 March 2015

Accepted after revision: 27 April 2015

Publication Date:
11 June 2015 (online)


Abstract

Iodofluorination of alkenes was performed by using IF5–pyridine–HF and a reductant such as potassium iodide or tin powder. The addition of IF to the double bond proceeded with stereo- and regioselectivity. In the reaction with internal alkenes, the trans-addition product was obtained selectively. With terminal alkenes, the addition took place regioselectively to give 1-iodo-2-fluoroalkanes.

Supporting Information