Oxidative C–C coupling of 2,6-di-tert-butylphenol in aqueous media via catalytically active molybdate surfactants

Abstract

Long-chain N-alkyliminodiacetatomolybdate catalytic surfactants can be incorporated within a CTAB micellar solution and have shown catalytic activity for the oxidation of 2,6-di-tert-butylphenol to the corresponding diphenoquinone in aqueous media. Scheme 1 Synthesis of molybdate surfactants. † Electronic supplementary information (ESI) available: Experimental details regarding synthesis of Na 2 MoO 3 C 12 IDA, determination of the CMC, catalysis conditions and measurement of DPQ. See

Investigation of 3d-transition metal acetates in the oxidation of substituted dioxolene and phenols

“…Various research groups have studied the oxidation of 2,6-DTBP using molecular oxygen [185][186][187][188][189]. H 2 O 2 or t BuOOH as oxidant to give two different oxidation products 3,3 -5,5 -tetra-tertbutyldiphenoquinone (DPQ) and 2,6-di-tert-butylbenzoquinone (BQ) [190,191].…”

Aerobic Oxidation of Phenols and Related Compounds using Carbon Nanotube–Gold Nanohybrid Catalysts

“…The reaction of 2,6-di-tert-butylphenol (7 b) led to the oxidative coupling of 7 b followed by further oxidation into dimeric 8 b (Entry 2). It is worth noting that the conversion took place at room temperature without any additional oxidant, as opposed to recent reports on the same transformation catalyzed by TiO 2 -supported gold nanoparticles, [18] molybdate surfactants, [19] or dicopper(II) complexes, [20] which all required H 2 O 2 and heating. 4-Methoxyphenol (7 c) was fully converted to ether 8 c within 24 h through an oxidative OÀC ortho-coupling (Entry 3) in lieu of the CÀC para-coupling observed in the above case.…”

A Metallomicellar Catalyst for Controlled Oxidation of Alcohols and Lignin Mimics in Water using Open Air as Oxidant

“…[58][59][60][61] Integration of both the catalyst component and the surfactant entity, in such a manner that the parts are covalently linked with each other as a single molecule, might offer a superior catalyst system. [62][63][64][65] This can exclude the necessity of the external addition of surfactant while bringing in the advantages of a unified in-built micellar system. Reports on such metallo-surfactant-based catalysts are scarce in the literature.…”

“…A suitable micellar entity accommodates the relevant organic substrates and oxidants in its hydrophobic core thereby bringing them closer and enhancing their reactivity [58–61] . Integration of both the catalyst component and the surfactant entity, in such a manner that the parts are covalently linked with each other as a single molecule, might offer a superior catalyst system [62–65] . This can exclude the necessity of the external addition of surfactant while bringing in the advantages of a unified in‐built micellar system.…”