Synthesis of α-Azido Ketones and Esters Using Recyclable Hypervalent Iodine Reagent

Abstract

A simple and mild method for the preparation of α-azido ketones and esters using hypervalent iodine reagent, 4,4′-bis-(dichloroiodo)-biphenyl, and sodium azide in 1,4-dioxane is discussed. Advantages of this system are easy workup, recyclable reagent, and moderate to good yields.

Keywords:

• α-Azido esters
• α-azido ketones
• 4,4′-bis-(dichloroiodo)-biphenyl
• recycle
• sodium azide

ACKNOWLEDGMENT

V. N. T. gratefully acknowledges All India Council for Technical Education (AICTE), India, for financial support under the Research Promotion Scheme (RPS).

Notes

^a Reaction conditions: substrate (5.0 mmol), 4,4′-bis-(dichloroiodo)-biphenyl (0.55 equiv), triethylamine (2.1 equiv), and sodium azide (2.1 equiv) in 1,4-dioxon (15 mL), reflux.

^b Starting compounds were prepared by standard literature procedures.

^c Isolated yields after column chromatography and structures were confirmed by comparison of IR and ¹H NMR with those of authentic materials.

^d No reaction.