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Open AccessArticle

Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones

Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland
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Academic Editor: Chryssostomos Chatgilialoglu
Molecules 2019, 24(22), 4184; https://doi.org/10.3390/molecules24224184
Received: 31 October 2019 / Revised: 10 November 2019 / Accepted: 11 November 2019 / Published: 18 November 2019
(This article belongs to the Special Issue Biomimetic Radical Chemistry and Applications)
The radical azidoalkylation of alkenes that was initially developed with α-iodoesters and α-iodoketones was extended to other activated iodomethyl derivatives. By using iodomethyl aryl sulfones, the preparation of γ-azidosulfones was easily achieved. Facile conversion of these azidosulfones to homoallylic azides using a Julia–Kocienski olefination reaction is reported, making the whole process equivalent to the azidoalkenylation of terminal alkenes. View Full-Text
Keywords: radical reaction; azidoalkylation; carboazidation; sulfones; azides; Julia–Kocienski olefination radical reaction; azidoalkylation; carboazidation; sulfones; azides; Julia–Kocienski olefination
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MDPI and ACS Style

Millius, N.; Lapointe, G.; Renaud, P. Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones. Molecules 2019, 24, 4184.

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