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Selective C-H Iodination of (Hetero)arenes

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2021 Jun 11
PMID 34114468
Citations 8
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Abstract

Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.

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References
1.
Tang R, Milcent T, Crousse B . Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol. J Org Chem. 2017; 83(2):930-938. DOI: 10.1021/acs.joc.7b02920. View

2.
Prakash G, Mathew T, Hoole D, Esteves P, Wang Q, Rasul G . N-halosuccinimide/BF3-H2O, efficient electrophilic halogenating systems for aromatics. J Am Chem Soc. 2004; 126(48):15770-6. DOI: 10.1021/ja0465247. View

3.
Tanwar L, Borgel J, Ritter T . Synthesis of Benzylic Alcohols by C-H Oxidation. J Am Chem Soc. 2019; 141(45):17983-17988. PMC: 6863597. DOI: 10.1021/jacs.9b09496. View

4.
Iida K, Ishida S, Watanabe T, Arai T . Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds. J Org Chem. 2019; 84(11):7411-7417. DOI: 10.1021/acs.joc.9b00769. View

5.
Racys D, Sharif S, Pimlott S, Sutherland A . Silver(I)-Catalyzed Iodination of Arenes: Tuning the Lewis Acidity of N-Iodosuccinimide Activation. J Org Chem. 2016; 81(3):772-80. DOI: 10.1021/acs.joc.5b02761. View