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• 128-39-2 2,6-di-tert-butylphenol 

Relevant academic research and scientific papers

A new approach to access difluoroalkylated diarylmethanes: Via visible-light photocatalytic cross-coupling reactions

Difluoroalkylated diarylmethanes with biological and pharmacological potentials were synthesized from para-quinone methides (p-QMs) and difluoroalkylating reagents via a visible light photocatalysis strategy. Mechanism studies showed that the excited photocatalyst, ?fac-Ir(ppy)3, was primarily quenched by p-QMs and the generated diarylmethane radical intermediates then underwent a radical-radical cross-coupling reaction with difluoroalkyl radicals. This reaction features mild conditions, high efficiency and wide functional group compatibility.

Iron-Catalyzed Ring Opening of Cyclopropanols and Their 1,6-Conjugate Addition to p-Quinone Methides

A novel iron-catalyzed ring opening of cyclopropanols and their 1,6-conjugate addition to p-quinone methides for accessing substituted phenols is disclosed. In this protocol, various cyclopropanols are converted to alkyl radicals and undergo 1,6-conjugate addition to p-quinone methides toward C–C bond formation. The salient features of this methodology include operationally simple and mild reaction conditions, environmentally benign protocol, high efficiency, inexpensive catalyst, good to excellent yield, and a wide range of substrate scope.

Organocatalytic Enantioselective 1,6-aza-Michael Addition of Isoxazolin-5-ones to p-Quinone Methides

A thiourea-Br?nsted base bifunctional catalyst allowed the enantioselective 1,6-aza-Michael addition of isoxazolin-5-ones to p-quinone methides to give isoxazolin-5-ones having a chiral diarylmethyl moiety attached to the N atom with fair to good yields and enantiomeric excesses. To the best of our knowledge this reaction represents the first example of enantioselective N-alkylation of isoxazolin-5-ones as well as the first example of enantioselective 1,6-aza-Michael reaction involving p-quinone methides.

TBAB-catalyzed 1,6-conjugate sulfonylation of paraquinone methides: A highly efficient approach to unsymmetrical gem-diarylmethyl sulfones in water ?

A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.

Visible-light-promoted radical cross-coupling of: Para-quinone methides with N-substituted anilines: An efficient approach to 2,2-diarylethylamines

An efficient protocol to access 2,2-diarylethylamines via visible-light-promoted radical reactions of para-quinone methides (p-QMs) with N-alkyl anilines has been disclosed. These reactions feature metal-free, redox-neutral, and mild reaction conditions with wide functional group compatibility.

Ammonium Chloride-Mediated Trifluoromethylthiolation of p-Quinone Methides

Ammonium chloride-mediated trifluoromethylthiolation of p-quinone methides is reported using inexpensive and bench stable AgSCF3 as a nucleophilic trifluoromethylthiolating (-SCF3) reagent. This method is an efficient strategy for the construction of the benzylic C(sp3)-SCF3 bond to synthesize trifluoromethylthio-diarylmethane derivatives by 1,6-conjugate addition/aromatization under mild reaction conditions without any metal catalyst, oxidants, or additives. This is the first report of trifluoromethylthiolation of p-quinone methides. In addition, di-trifluoromethylthiolation of δ-chloro-p-quinone methide and scalability are demonstrated.

Visible-Light-Enabled C?H Functionalization by a Direct Hydrogen Atom Transfer Uranyl Photocatalyst

The development of the uranyl cation as a powerful photocatalyst is seriously delayed in comparison with the advances in its fundamental and structural chemistry. However, its characteristic high oxidative capability in the excited state ([UO2]2+* (+2.6 V vs. SHE; SHE=standard hydrogen electrode) combined with blue-light absorption (hv=380–500 nm) and a long-lived fluorescence lifetime up to microseconds have reveals that the uranyl cation approaches an ideal photocatalyst for visible-light-driven organic transformations. Described herein is the successful use of uranyl nitrate as a photocatalyst to enable C(sp3)?H activation and C?C bond formation through hydrogen atom transfer (HAT) under blue-light irradiation. In particular, this operationally simple strategy provides an appropriate approach to the synthesis of diverse and valuable diarylmethane motifs. Mechanistic studies and DFT calculations have provided insights into the detailed mechanism of the photoinduced HAT pathway. This research suggests a general platform that could popularize promising uranyl photocatalytic performance.

Solvent-free microwave synthesis 4 - phenyl methylene - 2, 6 - di-tert-butyl - 2, 5 - cyclohexadiene -1 - ketone (by machine translation)

The invention discloses a 4 - benzylidene - 2, 6 - di-tert-butyl - 2, 5 - cyclohexadiene - 1 - ketone derivative (P -QM) green preparation method. Under the condition of using solvent-free microwave radiation heating, 2, 6 - di-tert-butyl phenol and aldehyde, through the Mannich condensation and [...] two-step reaction, to obtain the 4 - benzylidene - 2, 6 - di-tert-butyl - 2, 5 - cyclohexadiene - 1 - ketone derivative (P -QM). This method has the raw material is cheap, the atom economy is high, fast reaction time, environment friendly, without the use of hazardous reagent and solvent, synthetic step is simple and convenient and the like, and the mild reaction conditions, substrate range wide applicability, simple and safe operation, and is suitable for industrial production. (by machine translation)

Visible-light mediated trifluoromethylation of p-quinone methides by 1,6-conjugate addition using pyrylium salt as organic photocatalyst

A transition metal free visible light mediated organo photoredox catalyzed trifluoromethylation of p-quinone methides (p-QMs) to construct fluoro-analogs of dichlorodiphenyltrichloroethane (DDT) is reported using a bench stable, inexpensive Langlois reagent as a trifluoromethyl radical source. This protocol could generate a benzylic C(sp3)-CF3 bond with excellent yield under mild reaction conditions using 1,6-conjugate addition/aromatization of trifluoromethyl radical in the absence of any external additives. Further, we demonstrate di-trifluoromethylation and gram scale synthesis of this reaction.

Unravelling the Nucleophilicity of Butenolides for 1,6-Conjugate Addition to p-Quinone Methides: A Direct Access to Diversely Substituted Butenolide-Derived Diarylmethanes

A Lewis acid catalyzed regioselective C-C bond is constructed through β-addition of deconjugated butenolides with p-quinone methides in a 1,6-conjugate addition manner. Interestingly, Lewis acid catalyzed vinylogous Mukaiyama-Michael reaction of silyloxyfurans with p-QMs proceeds selectively through the α or γ position exclusively. The reaction is mild with broad substrate scope, thus allowing easy access to a wide range of bis-arylated α-/β-/γ-substituted butenolides.