Synthesis 2010(22): 3879-3882  
DOI: 10.1055/s-0030-1258250
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regiospecific Azidoiodination of Alkenes with Sodium Periodate, Potassium Iodide, and Sodium Azide: A High-Yield Synthesis of β-Iodoazides

Pandurang V. Chouthaiwale, Pratibha U. Karabal, Gurunath Suryavanshi, Arumugam Sudalai*
Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411 008, India
Fax: +91(20)25902676; e-Mail: a.sudalai@ncl.res.in;
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Publikationsverlauf

Received 19 July 2010
Publikationsdatum:
14. September 2010 (online)

Abstract

The combination of sodium periodate, potassium iodide, and sodium azide has been found to be an efficient, simple, and inexpensive reagent system for azidoiodination of alkenes. The regiospecific 1,2-azidoiodination proceeds in an anti-Markovnikov fashion to produce β-iodoazides in excellent yields.