Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes

被引：11

作者：

Misal, Balu ^{[1
,2
]}

Palav, Amey ^{[1
,2
]}

Ganwir, Prerna ^{[1
]}

Chaturbhuj, Ganesh ^{[1
]}

机构：

[1] Inst Chem Technol, Mumbai 400019, Maharashtra, India

[2] Loba Chem Pt Ltd, Res & Dev Ctr, Tarapur 401506, Thane, India

来源：

TETRAHEDRON LETTERS | 2021年 / 74卷

关键词：

NIS; Sulfated polyborate; Iodination; Substituted arenes; SOLVENT-FREE SYNTHESIS; AROMATIC-COMPOUNDS; REGIOSELECTIVE IODINATION; HYDROGEN-PEROXIDE; ENVIRONMENTALLY BENIGN; IODINE MONOCHLORIDE; EFFICIENT CATALYST; FULLERS EARTH; FREE PROTOCOL; BROMINATION;

D O I：

10.1016/j.tetlet.2021.153154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页数：7

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