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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2010 - Issue 1
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Original Articles

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

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Pages 131-135 | Received 19 Sep 2009, Published online: 14 Dec 2010
 

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.

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.

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