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Nonreductive Deiodination of ortho-Iodo-Hydroxylated Arenes Using Tertiary Amines

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Rahul Subhash Talekar,^† Grace Shiahuy Chen,^‡ Shin-Yu Lai,^† and Ji-Wang Chern*^†

School of Pharmacy, College of Medicine, National Taiwan University, No. 1, Section 1, Jen-Ai Road, Taipei, Taiwan, ROC, and Department of Applied Chemistry, Providence University, 200 Chung-Chi Road, Shalu, Taichung, ROC chern@jwc.mc.ntu.edu.tw

J. Org. Chem., 2005, 70 (21), pp 8590–8593

DOI: 10.1021/jo051191x

Publication Date (Web): September 21, 2005

†

National Taiwan University.

‡

Providence University.

Author to whom correspondence should be addressed. Phone: 886-2-23939462. Fax: 886-2-23934221.

Abstract

A convenient and nonreductive deiodination is reported for the ortho-iodo-hydroxylated arenes including derivatives of quinolinol, phenol, and naphthol. Tertiary amines pyridine, triethylamine, and N-methylmorpholine in the presence of water initiated deiodination of ortho-iodo-hydroxylated arenes without affecting para-iodine and other reduction-susceptible groups. This reported method also works efficiently for polyiodinated systems. Simplicity, short reaction times, and absence of reducing catalyst are features of this method.

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Published In Issue October 14, 2005
Received June 13, 2005

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Nonreductive Deiodination of ortho-Iodo-Hydroxylated Arenes Using Tertiary Amines

Abstract

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History

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Related Content

Iodothyronine Deiodinase Mimics. Deiodination of o,o‘-Diiodophenols by Selenium and Tellurium Reagents

A Concise Total Synthesis of (−)-Quinocarcin via Aryne Annulation

Number 87

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