An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides

Trisha Banik; Vipul V Betkekar; Krishna P Kaliappan

doi:10.1002/asia.201801454

An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides

Chem Asian J. 2018 Dec 4;13(23):3676-3680. doi: 10.1002/asia.201801454. Epub 2018 Oct 23.

Authors

Trisha Banik¹, Vipul V Betkekar¹, Krishna P Kaliappan¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-, 400076, India.

PMID: 30280503
DOI: 10.1002/asia.201801454

Abstract

A direct transformation of ortho-alkynylated aromatic vinyl ethers to 1-iodonaphthalenes and other iodo-heterocycles under mild Lewis acidic conditions in the presence of iodide as an external nucleophile is reported. The first example of an iodoannulation strategy using a nucleophilic source of iodine, coupled with good to excellent yields, exclusive alpha regioselectivity and a broad substrate scope makes this work an attractive avenue towards the construction of aromatic iodides.

Keywords: 6-exo-trig cyclization; Lewis acid-mediated cyclization; aromatic iodides; aromatization; iodoannulation.

Abstract

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