94876-25-2

Upstream product

• 1020-31-1 3,5-Di-tert-butylcatechol 
• 62-53-3 aniline 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 718598-14-2 C₂₁H₂₉NO 
• 457604-98-7 Pt(o-amidophenolato)(2,2'-bipyridine) 
• 457604-97-6 Pd(o-amidophenolato)(2,2-bipyridine) 
• 1017968-88-5 Co(2-anilino-4,6-di-tert-butylphenolate)2 
• 1207294-92-5 5,7-di-tert-butyl-3-phenylbenzoxazolium tetrafluoroborate 

Relevant academic research and scientific papers

Synthesis of N,O-heterocyclic carbene and coordination to rhodium(I) and copper(I)

5,7-Di-tert-butyl-3-phenyl benzoxazolium tetrafluoroborate 1 could be prepared by simple reaction of the corresponding aminophenol with triethyl orthoformate under acidic conditions. Both rhodium(I) and copper(I) complexes with benzoxazol-2-ylidene ligand

Copper-Catalyzed Aziridination with Redox-Active Ligands: Molecular Spin Catalysis

Small-molecule catalysts as mimics of biological systems illustrate the chemists’ attempts at emulating the tantalizing abilities displayed by nature's metalloenzymes. Among these innate behaviors, spin multistate reactivity is used by biological systems as it offers thermodynamic leverage towards challenging chemical reactivity but this concept is difficult to translate into the realm of synthetic organometallic catalysis. Here, we report a rare example of molecular spin catalysis involving multistate reactivity in a small-molecule biomimetic copper catalyst applied to aziridination. This behavior is supported by spin state flexibility enabled by the redox-active ligand.

Circumventing Intrinsic Metal Reactivity: Radical Generation with Redox-Active Ligands

Nickel complexes have gained sustained attention as efficient catalysts in cross-coupling reactions and co-catalysts in dual systems due to their ability to react with radical species. Central to this reactivity is nickel's propensity to shuttle through several accessible redox states from Ni0 to NiIV. Here, we report the catalytic generation of trifluoromethyl radicals from a nickel complex bearing redox-active iminosemiquinone ligands. This unprecedented reactivity is enabled through ligand-based oxidation performing electron transfer to an electrophilic CF3+ source while the nickel oxidation state is preserved. Additionally, extension of this reactivity to a copper complex bearing a single redox equivalent is reported, thus providing a unified reactivity scheme. These results open new pathways in radical chemistry with redox-active ligands.

C?N Bond Formation from a Masked High-Valent Copper Complex Stabilized by Redox Non-Innocent Ligands

The reactivity of a stable copper(II) complex bearing fully oxidized iminobenzoquinone redox ligands towards nucleophiles is described. In sharp contrast with its genuine low-valent counterpart bearing reduced ligands, this complex performs high-yielding C?N bond formations. Mechanistic studies suggest that this behavior could stem from a mechanism akin to reductive elimination occurring at the metal center but facilitated by the ligand: it is proposed that a masked high oxidation state of the metal can be stabilized as a lower copper(II) oxidation state by the redox ligands without forfeiting its ability to behave as a high-valent copper(III) center. These observations are substantiated by a combination of advanced EPR spectroscopy techniques with DFT studies. This work sheds light on the potential of redox ligands as promoters of unusual reactivities at metal centers and illustrates the concept of masked high-valent metallic species.

Iminosemiquinone radical ligands enable access to a well-defined redox-active CuII-CF3 complex

The reaction of a copper complex bearing iminosemiquinone ligands with a CF3+ source provides an unprecedented Cu II-CF3 complex through ligand-based oxidation. Reactivity of this complex leads to nucleophilic trifluoromethylation of the ligand, suggesting an electronic interplay that results in a formal umpolung of the initial CF3+. This journal is the Partner Organisations 2014.

Synthesis and study of antiviral and anti-radical properties of aminophenol derivatives

A number of sterically-hindered o-aminophenol derivatives have been synthesized, and their antiviral activity in parallel with reactivity towards commonly encountered free-radical intermediates was investigated. Of the compounds tested, the highest activity in suppressing replication of Herpes simplex type l viruses was displayed by N-acyl and N-aryl derivatives of 4,6-di-tert-butyl-2-aminophenol, which were able to interact with organic free radicals and, at the same time, manifested low reactivity towards reactive oxygen species.

Electronic Structure of Bis(o-iminobenzosemiquinonato)metal Complexes (Cu, Ni, Pd). The Art of Establishing Physical Oxidation States in Transition-Metal Complexes Containing Radical Ligands

The ligand 2-anilino-4,6-di-tert-butylphenol and its 2-(3,5-dichloroanilino)-4,6-di-tert-butylphenol analogue react in CH3CN or CH3OH solutions with divalent transition metal ions in the presence of air and triethylamine. Depending o

Synthesis and Antioxidant Properties of Some Derivatives of Alkylated Pyrocatechol

Alkylated 1,3-benzodioxane, 1,3-benzoxathiole, o-aminophenols, and 2,3-dihydro-1,3-benzoxazoles were obtained from 3,5-di-tert-butylbenzene-1,2-diol. The antiradical and antioxidant activities of these compounds were examined in the model oxidation of hexane, initiated by γ irradation. The antiradical activity of the ortho analog of tocopherol with a five-membered ring, 7-hydroxy-4,6-di-tert-butyl-1,3-benzoxathiole-2-thione, exceeds fourfold that of the six-membered analog, 8-hydroxy-5,7-di-tert-butyl-1,3-benzodioxane.