Development of 3,5-Di-tert-butylphenol as a Model Substrate for Biomimetic Aerobic Copper Catalysis

Kwon, Ohhyeon; Esguerra, Kenneth Virgel N.; Glazerman, Michael; Petitjean, L.; Xu, Ya-Lun; Ottenwaelder, Xavier; Lumb, Jean‐Philip

doi:10.1055/s-0036-1588761

Synlett

2017

DOI: 10.1055/s-0036-1588761

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Development of 3,5-Di-tert-butylphenol as a Model Substrate for Biomimetic Aerobic Copper Catalysis

Ohhyeon Kwon

Kenneth Virgel N. Esguerra

Michael Glazerman

et al.

Abstract: We develop 3,5-di-tertbutylphenol as a strategic substrate for the evaluation of biomimetic Cu2–O2 complexes intended to mimic the activity of tyrosinase. We describe a practical and scalable synthesis and validate its use in an aerobic ortho-oxygenation catalyzed by N,N′-di-tert-butylethylenediamine and [Cu(CH3CN)4]PF6.

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2024

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Cited by 4 publications

References 13 publications

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Selective Aerobic C–H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles

Liu

Qian

et al. 2017

Org. Lett.

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Using O as the oxidant, the benzoxazole frameworks can be directly constructed from the readily available phenols and primary amines in the presence of NHPF over copper under mild conditions. Mechanistic studies showed that a novel mechanism involving biphenyldiols and o-quinones very possibly takes effect in the reaction, because both can selectively give the benzoxazoles under the reaction conditions. An unprecedented unstrained C-C bond cleavage takes place in the reaction.

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Selective Aerobic C–H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles

Liu

Qian

et al. 2017

Org. Lett.

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Cluster Preface: Catalytic Aerobic Oxidations

Stahl

Rovis

2017

Synlett

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Shannon S. Stahl was an undergraduate at the University of Illinois at Urbana-Champaign, and a graduate student at Caltech (PhD, 1997), where he worked with Professor John Bercaw. He was an NSF postdoctoral fellow with Professor Stephen Lippard at Massachusetts Institute of Technology from 1997–1999. He is currently a Professor of Chemistry at the University of Wisconsin–Madison, where he began his independent career in 1999. His research group specializes in catalysis, with an emphasis on aerobic oxidation reactions and oxygen chemistry related to energy conversion. Tomislav Rovis was born in Zagreb in former Yugoslavia but was largely raised in southern Ontario, Canada. He earned his PhD degree at the University of Toronto (Canada) in 1998 under the direction of Professor Mark Lautens. From 1998–2000, he was an NSERC Postdoctoral Fellow at Harvard University (USA) with Professor David A. Evans. In 2000, he began his independent career at Colorado State University and was promoted in 2005 to Associate Professor and in 2008 to Professor. His group’s accomplishments have been recognized by a number of awards including an Arthur C. Cope Scholar, an NSF CAREER Award, a Fellow of the American Association for the Advancement of Science and a Katritzky Young Investigator in Heterocyclic Chemistry. In 2016, he moved to Columbia University where he is currently Professor of Chemistry.

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A 1,4-benzoquinone with counteracting inductive donor and acceptor substituents

Palidwar,

Hahn,

Boeré

2024

Can. J. Chem.

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Investigation of a published route to produce 3,5-di- tert-butylphenol, starting from commercial 3,5-di- tert-butylbenzoic acid via 3,5-di- tert-butylanlinium hydrogen sulfate, unexpectedly yielded 2,6-dintitro-3,5-di- tert-butylphenol. Attempts to increase the yield of the latter resulted, instead, in the previously unreported 2,6-dinitro-3,5-di- tert-butylcyclohexa-2,5-dien-1,4-dione. Single-crystal X-ray diffraction structures are reported for the anilinium salt, the nitrated phenol, and the quinone. Voltammetry of the quinone shows two chemically reversible reductions in anhydrous solution and the radical anion produced from the first reduction step has been characterized by electron paramagnetic resonance spectroscopy. This compound fits well to the middle range of electron-poor quinones, indicating that the inductive effects of the tert-butyl and nitro groups counteract each other. This conclusion is also supported by the infrared spectroscopic data where the ν(C=O) and ν(C=C) bands are of very similar energy to those of 2,3,5,6-tetrachloro-1,4-benzoquinone.

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Development of 3,5-Di-tert-butylphenol as a Model Substrate for Biomimetic Aerobic Copper Catalysis

Cited by 4 publications

References 13 publications

Selective Aerobic C–H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles

Selective Aerobic C–H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles

Cluster Preface: Catalytic Aerobic Oxidations

A 1,4-benzoquinone with counteracting inductive donor and acceptor substituents

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