138308-53-9Relevant academic research and scientific papers
Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols
Heid, Berenice,Plietker, Bernd
, p. 340 - 350 (2016)
The iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the intermolecular allylation of naphthol derivatives to give the corresponding partially dearomatized allylated chromenones in good to excellent yields. The scope and limitations are reported. An efficient decarboxylative intramolecular C-allylation, starting from allyl naphthyl carbonates, was developed. From a mechanistic point of view, the overall process is the result of a fast O-allylation followed by a sigmatropic rearrangement to the desired product.
Iron-catalyzed dioxygen-driven C-C bond formation: Oxidative dearomatization of 2-naphthols with construction of a chiral quaternary stereocenter
Oguma, Takuya,Katsuki, Tsutomu
supporting information, p. 20017 - 20020 (2013/02/22)
Iron(salan) complex 1 was found to catalyze the oxidative dearomatization of 1-substituted 2-naphthols with the formation of an all-carbon quaternary stereocenter in air in the presence of nitroalkanes, to afford the corresponding cyclic enones with high enantioselectivity of 88-96% ee.
A comparative Study of the Decomposition of o-Alkynyl-Substituted Aryl Diazo Ketones. Synthesis of Polysubstituted β-Naphthols via Arylketene Intermediates
Padwa, Albert,Chiacchio, Ugo,Fairfax, David J.,Kassir, Jamal J.,Litrico, Angelo,at al.
, p. 6429 - 6437 (2007/10/02)
The photochemical, thermal, and rhodium-catalyzed decomposition reactions of several closely related o-alkynyl or o-alkenyl α-diazoaceto- and propiophenone derivatives have been studied.The reaction outcome is markedly dependent upon the reaction conditions employed for nitrogen extrusion.Thermolysis or photolysis of o-alkynyl α-diazopropiophenone derivatives yields polysubstituted β-naphthols.These products are derived from Wolff rearrangement of the initially formed carbene to give an aryl ketene which undergoes intramolecular cyclization onto the o-alkynylsubstituent.In direct contrast to the thermal and photochemical results, Rh(II)-catalyzed decomposition yields products derived from direct attack of a rhodium carbenoid onto the tethered ?-system producing a vinyl carbenoid intermediate.Further reaction of the cyclized carbenoid with the starting diazo compound furnished a vinyl indenone which undergoes a rapid intramolecular Diels-Alder reaction to produce a novel dimer whose structure was elucidated by an X-ray crystal analysis.Replacement of the methyl group on the diazo center with a sterically less demanding hydrogen atom was also found to play an important role in controlling the outcome of the Rh(II)-catalyzed reaction.
Rearrangement of o-alkynyl substituted α-diazoacetophenones. Conversion to β-naphthols via arylketene intermediates
Padwa,Austin,Chiacchio,Kassir,Rescifina,Xu
, p. 5923 - 5926 (2007/10/02)
In contrast to the rhodium (II) mediated cycloisomerization of o-alkynyl substituted α-diazoacetophenones, irradiation leads to β-naphthols which are formed via cyclization of an arylketene intermediate.
