Synthesis 2016; 48(09): 1353-1358
DOI: 10.1055/s-0035-1561374
paper
© Georg Thieme Verlag Stuttgart · New York

Iodoazidation of Alkenes by Using Iodine Pentafluoride–Pyridine–Hydrogen Fluoride and Trimethylsilyl Azide

Tatsuki Hiraoka
Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan   Email: shara@eng.hokudai.ac.jp
,
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: 11 January 2015

Accepted after revision: 17 January 2016

Publication Date:
15 February 2016 (online)


Abstract

Iodoazidation of alkenes was carried out by using iodine pentafluoride–pyridine–hydrogen fluoride and trimethylsilyl azide. In the reactions of terminal alkenes, anti-Markovnikov products were formed selectively. Cyclohexene gave a mixture of cis- and trans-adducts. These results suggest the involvement of radical species in the reaction.

Supporting Information