Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines

Michael T Shea; Gregory T Rohde; Yulia A Vlasenko; Pavel S Postnikov; Mekhman S Yusubov; Viktor V Zhdankin; Akio Saito; Akira Yoshimura

doi:10.3390/molecules26237355

Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines

Molecules. 2021 Dec 3;26(23):7355. doi: 10.3390/molecules26237355.

Authors

Michael T Shea¹, Gregory T Rohde², Yulia A Vlasenko³, Pavel S Postnikov³, Mekhman S Yusubov³, Viktor V Zhdankin¹, Akio Saito⁴, Akira Yoshimura^{1

3}

Affiliations

¹ Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA.
² Marshall School, Duluth, MN 55811, USA.
³ Research School of Chemisty and Applied Biomediacl Sciences, The Tomsk Polytechnic University, 634050 Tomsk, Russia.
⁴ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan.

Abstract

Hypervalent iodine heterocycles represent one of the important classes of hypervalent iodine reagents with many applications in organic synthesis. This paper reports a simple and convenient synthesis of benziodazolones by the reaction of readily available iodobenzamides with m-chloroperoxybenzoic acid in acetonitrile at room temperature. The structure of one of these new iodine heterocycles was confirmed by X-ray analysis. In combination with PPh₃ and pyridine, these benziodazolones can smoothly react with alcohols or amines to produce the corresponding esters or amides of 3-chlorobenzoic acid, respectively. It was found that the novel benziodazolone reagent reacts more efficiently than the analogous benziodoxolone reagent in this esterification.

Keywords: aroylation; benziodazolone; hypervalent iodine; iodine heterocycles.

Abstract

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