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
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Publikationsverlauf

Received: 11. Januar 2015

Accepted after revision: 17. Januar 2016

Publikationsdatum:
15. Februar 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.

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