Iodobenzene Dichloride in Combination with Sodium Azide for the Effective Synthesis of Carbamoyl Azides from Aldehydes

Abstract

Various aliphatic and aromatic aldehydes are converted into their corresponding carbamoyl azides in good to excellent yields with the use of a combined reagent system of iodobenzene dichloride and sodium azide in acetonitrile under nitrogen.

Key words

aldehydes - carbamoyl azides - hypervalent iodine - iodobenzene­ dichloride - oxidations

References

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22

When n-heptanal was treated with 1.2 equiv of PhICl₂ and 2.4 equiv of NaN₃, the yield of hexylcarbamoyl azide decreased to 75%, which was 19% lower than that with 2.0 equiv of PhICl₂ and 4.0 equiv of NaN₃ under the otherwise same reaction conditions (Table  [¹] , entry 5). Thus, in order to obtain the excellent outcome within the shorter time period and taking into account that both PhICl₂ and NaN₃ are readily available and cost-effective, 2 equiv of PhICl₂ and 4 equiv of NaN₃ were used in the subsequent work.