Artificial nonheme iron and manganese oxygenases for enantioselective olefin epoxidation and alkane hydroxylation reactions

Jie Chen, Zhankun Jiang, Shunichi Fukuzumi, Wonwoo Nam, Bin Wang

Research output: Contribution to journalReview articlepeer-review

87 Scopus citations

Abstract

The development of sustainable enantioselective olefin epoxidation and alkane oxidation reactions under environmentally friendly conditions is an ultimate goal that has long been pursued in chemistry. Excellent examples are naturally occurring monooxygenases, which are able to catalyze a variety of biological oxidation reactions using molecular oxygen (O2) that afford high chemo-, regio-, and/or stereoselectivities. Inspired by the oxidation reactions of iron-containing monooxygenases, substantial efforts have been made towards the development of efficient catalysis for the enantioselective oxidation of hydrocarbons using bioinspired nonheme iron and manganese catalysts under mild conditions. In this review, we describe synthetic models that functionally mimic these monooxygenases. There are a large number of nonheme iron and manganese complexes that can epoxidize olefins with high enantioselectivities, whereas only a few examples are reported for nonheme iron- and manganese-catalyzed enantioselective oxidation of inert C(sp3)–H bonds. In addition to its great achievement for synthetic applications, mechanistic studies in biomimetic oxidation systems have also been intensively investigated, providing important insights into the understanding of the nature of active oxidants and the formation of the intermediates via O[sbnd]O bond activation and the design of more elegant biomimetic oxidation catalysts. Thus, these bioinspired nonheme iron and manganese complexes used as catalysts in the enantioselective C[dbnd]C epoxidation and aliphatic C(sp3)–H oxidation are the focus of discussion in this review.

Original languageEnglish
Article number213443
JournalCoordination Chemistry Reviews
Volume421
DOIs
StatePublished - 15 Oct 2020

Bibliographical note

Funding Information:
We acknowledge financial support of this work from the National Natural Science Foundation of China (21771087 to B.W. and 21703080 to J.C.), the NSF of Shandong Province (ZR2017MB007 to B.W. and ZR2017BB010 to J.C.), Taishan Scholar Program of Shandong Province (tsqn201812078 to B.W.), the NRF of Korea through CRI(NRF-2012R1A3A2048842 to W.N.), the Basic Science Research Program (2017R1D1A1B03032615 to S.F.) and by MEXT (Grant-in-Aid16H02268 to S.F.).

Publisher Copyright:
© 2020 Elsevier B.V.

Keywords

  • Bioinspired catalysis
  • Enantioselective epoxidation and hydroxylation
  • Mechanism
  • Nonheme iron and manganese catalysts

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