4.8 Article

Electrochemical Organoselenium-Catalyzed Intermolecular Hydroazolylation of Alkenes with Low Catalyst Loadings

Journal

ORGANIC LETTERS
Volume 24, Issue 29, Pages 5345-5350

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01983

Keywords

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Funding

  1. National Natural Science Foundation of China [21871019, 2217011202]
  2. Beijing Municipal Education Committee Project [KZ202110005003, KM202110005006]
  3. Beijing Natural Science Foundation [2222003]

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This paper reports a new method for the hydroazolylation of alkenes with azoles under external oxidant-free conditions with low catalyst loadings.
The organoselenium-catalyzed amination of alkenes is a promising way to construct functionalized amines. However, the use of chemical oxidants and the unavoidable formation of allylic amine or enamine are the two main limitations of these methodologies. Against this background, we herein report an electro-selenocatalytic regime for the hydroazolylation of alkenes with azoles under external oxidant-free conditions with low catalyst loadings. Moreover, this protocol enables the generation of amines without vinyl substituents.

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