ArticleAngewandte Chemie (International ed. in English)2019
Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 30 citations in OpenAlex.
- The Oxidation of Electron-Rich Arenes Using a HACS omega · 2024Article
- A decade of lessons in the activation of ArILChemical science · 2024Review
- Oxidation of Electron-Deficient Phenols Mediated by Hypervalent Iodine(V) Reagents: Fundamental Mechanistic Features Revealed by a Density Functional Theory-Based Investigation.The Journal of organic chemistry · 2021Article
- Bidentate Nitrogen-Ligated I(V) Reagents, Bi(The Journal of organic chemistry · 2021Article
- Recent Advances in the Selective Oxidative Dearomatization of Phenols toSynlett : accounts and rapid communications in synthetic organic chemistry · 2021Article
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Authors and funding
3 authors at 2 institutions in 1 country.
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Abstract
Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.
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