Seeing the cis-Dihydroxylating Intermediate: A Mononuclear Nonheme Iron-Peroxo Complex in cis-Dihydroxylation Reactions Modeling Rieske Dioxygenases

Wenjuan Zhu, Akhilesh Kumar, Jin Xiong, Macon J. Abernathy, Xiao Xi Li, Mi Sook Seo, Yong Min Lee, Ritimukta Sarangi, Yisong Guo, Wonwoo Nam

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The nature of reactive intermediates and the mechanism of the cis-dihydroxylation of arenes and olefins by Rieske dioxygenases and synthetic nonheme iron catalysts have been the topic of intense research over the past several decades. In this study, we report that a spectroscopically well characterized mononuclear nonheme iron(III)-peroxo complex reacts with olefins and naphthalene derivatives, yielding iron(III) cycloadducts that are isolated and characterized structurally and spectroscopically. Kinetics and product analysis reveal that the nonheme iron(III)-peroxo complex is a nucleophile that reacts with olefins and naphthalenes to yield cis-diol products. The present study reports the first example of the cis-dihydroxylation of substrates by a nonheme iron(III)-peroxo complex that yields cis-diol products.

Original languageEnglish
Pages (from-to)4389-4393
Number of pages5
JournalJournal of the American Chemical Society
Volume145
Issue number8
DOIs
StatePublished - 1 Mar 2023

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