Journal
TETRAHEDRON LETTERS
Volume 74, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153154
Keywords
NIS; Sulfated polyborate; Iodination; Substituted arenes
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Funding
- Loba Chemie Pvt. Ltd.
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A sulfated polyborate catalyst has been developed for efficient iodination of arenes with high regioselectivity and yield. This method is versatile for mono and diiodination of various substrates, including the synthesis of intermediates for thyroid treatment drugs and specialty chemicals.
Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products. (C) 2021 Elsevier Ltd. All rights reserved.
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