Practical regio- and stereoselective azidation and amination of terminal alkenesElectronic supplementary information (ESI) available: Experimental details, procedures, 1H NMR & 13C NMR spectra, and HRMS. See DOI: 10.1039/c8ob02734j

There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily avail...

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Bibliographic Details
Main Authors Ojo, Olatunji S, Miranda, Octavio, Baumgardner, Kyle C, Bugarin, Alejandro
Format Journal Article
LanguageEnglish
Published 12.12.2018
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Summary:There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear ( E )-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields. A metal-free synthesis of allylic azides and allylic amines was achieved under mild reaction conditions, which represents a milder alternative for azidation and amination reactions.
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Electronic supplementary information (ESI) available: Experimental details, procedures
C NMR spectra, and HRMS. See DOI
10.1039/c8ob02734j
H NMR
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02734j