Preparation, Structure, and Reactivity of Bicyclic Benziodazole: a New Hypervalent Iodine Heterocycle

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2018 Jul 7

PMID 29977373

Citations 5

Authors

Akira Yoshimura

Michael T Shea

Cody L Makitalo

Melissa E Jarvi

Gregory T Rohde

Akio Saito

Mekhman S Yusubov

Viktor V Zhdankin

Affiliations

Soon will be listed here.

Abstract

A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-diisopropylisophthalamide with -chloroperoxybenzoic acid under mild conditions. Single crystal X-ray crystallography of this compound revealed a five-membered bis-heterocyclic structure with two covalent bonds between the iodine atom and the nitrogen atoms. This novel benziodazole is a very stable compound with good solubility in common organic solvents. This compound can be used as an efficient reagent for oxidatively assisted coupling of carboxylic acids with alcohols or amines to afford the corresponding esters or amides in moderate yields.

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