1076-26-2Relevant articles and documents
ORTHO-METHYLATION OF PHENOLS WITH ETHYL(IODOMETHYL)ZINC
Lehnert, Erich K.,Sawyer, J. Scott,Macdonald, Timothy L.
, p. 5215 - 5218 (1989)
The regioselective ortho-methylation of phenols by in situ generated ethyl(iodomethyl)zinc via an internal alkylation process is described.
Stereoselective synthesis of disubstituted naphthalene-1,2- oxides
Tius,Reddy
, p. 859 - 869 (1994)
Spiroepoxy naphthalenones, obtained from the stereoselective oxidation of 2-hydroxyalkyl-1-naphthols with sodium periodate, were converted to naphthalene-1,2-oxides by reaction with methyllithium followed by Payne rearrangement.
Photocatalytic Systems with Flavinium Salts: From Photolyase Models to Synthetic Tool for Cyclobutane Ring Opening
Hartman, Tomá?,Cibulka, Radek
, p. 3710 - 3713 (2016)
Two new photocatalytic systems based on flavinium species formed in situ by protonation of riboflavin-tetraacetate (1) with triflic acid or prepared in advance via alloxazine quaternization are presented as effective tools for oxidative cyclobutane ring [2 + 2] cycloreversion using visible light. The system with 1,3-dimethyl-8-trifluoromethylalloxazinium perchlorate (2c) was found to be superior allowing an acid-free mild procedure, which results in the opening of cyclobutanes with high oxidation potential (up to 2.14 V) and/or with sensitive groups (e.g., furan) without side reactions.
Organocatalytic Asymmetric Dearomatization Reaction for the Synthesis of Axial Chiral Allene-Derived Naphthalenones Bearing Quaternary Stereocenters
Woldegiorgis, Alemayehu Gashaw,Han, Zhao,Lin, Xufeng
, p. 6606 - 6611 (2021)
The highly regio-, diastereo-, and enantioselective dearomatization reaction of 1-substituted 2-naphthols and β,γ-alkynyl-α-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and effici
Phase-Transfer-Catalyzed Oxaziridine-Mediated Hydroxylative Phenol and Naphthol Dearomatization
Grandclaudon, Charlotte,Toullec, Patrick Y.
, p. 260 - 264 (2016)
A new methodology for the dearomative ortho-hydroxylation of substituted phenolic substrates is reported. In the presence of a phase-transfer catalyst and a base, N-sulfonyloxaziridines react with phenols to give the corresponding 6-alkyl-6-hydroxycyclohe
Oxidation of 2-substituted cycloalkanones with cerium(IV) sulfate tetrahydrate in alcohols and acetic acid
He, Liangyou,Horiuchi, C. Akira
, p. 2515 - 2521 (1999)
The reaction of 2-substituted cycloalkanones with cerium(IV) sulfate tetrahydrate (CS) in alcohols and acetic acid gave the corresponding alkyl esters of oxo acids (80-96%) and oxo acids (78-96%), respectively, by oxidative cleavage of the C(R).C=O bond. In the case of 2-iodocycloalkanones in methanol, the dimethyl ester was obtained in good yield. A treatment of 5α-cholestan-3-one with CS in methanol produced 2-acetal 3-ester of 2,3-seco derivative in good yield. The effects of cerium(IV) and copper(II) salts are also discussed.
Site-selective Oxidative Dearomatization of Phenols and Naphthols into ortho-Quinols or Epoxy ortho-Quinols using Oxone as the Source of Dimethyldioxirane
Cabrera-Afonso, María J.,Carre?o, M. Carmen,Urbano, Antonio
supporting information, (2019/08/21)
A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho-quinols or epoxy ortho-quinols from a site-selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key step. (Figure presented.).
NAPHTHALENE-CONTAINING POLYMERS AND METHODS OF MAKING THE SAME
-
Paragraph 0021; 0081-0082, (2018/08/09)
The present disclosure relates to a dimer that includes a first hydroxyl-functionalized naphthalene group and a second hydroxyl-functionalized naphthalene group, where the first hydroxyl-functionalized naphthalene group and the second hydroxyl-functionalized naphthalene group are connected by a bridging group. The present disclosure also relates to a polymer synthesized using the dimer, as well as methods for synthesizing both the dimer and the polymer.
Intermediacy of Ni-Ni Species in sp2 C-O Bond Cleavage of Aryl Esters: Relevance in Catalytic C-Si Bond Formation
Somerville, Rosie J.,Hale, Lillian V. A.,Gómez-Bengoa, Enrique,Burés, Jordi,Martin, Ruben
supporting information, p. 8771 - 8780 (2018/06/25)
Monodentate phosphine ligands are frequently employed in the Ni-catalyzed C-O functionalization of aryl esters. However, the extensive body of preparative work on such reactions contrasts with the lack of information concerning the structure and reactivity of the relevant nickel intermediates. In fact, experimental evidence for a seemingly trivial oxidative addition into the C-O bond of aryl esters with monodentate phosphines and low-valent nickel complexes still remains elusive. Herein, we report a combined experimental and theoretical study on the Ni(0)/PCy3-catalyzed silylation of aryl pivalates with CuF2/CsF additives that reveals the involvement of unorthodox dinickel oxidative addition complexes in C-O bond cleavage and their relevance in C-Si bond formation. We have obtained a mechanistic picture that clarifies the role of the additives and demonstrates that dinickel complexes act as reservoirs of the propagating monomeric nickel complexes by disproportionation. We believe this study will serve as a useful entry point to unravelling the mechanistic underpinnings of other related Ni-catalyzed C-O functionalization reactions employing monodentate phosphines.
Manganese-Catalyzed Aminomethylation of Aromatic Compounds with Methanol as a Sustainable C1 Building Block
Mastalir, Matthias,Pittenauer, Ernst,Allmaier, Günter,Kirchner, Karl
supporting information, p. 8812 - 8815 (2017/07/12)
This study represents the first example of a manganese-catalyzed environmentally benign, practical three-component aminomethylation of activated aromatic compounds including naphtols, phenols, pyridines, indoles, carbazoles, and thiophenes in combination with amines and MeOH as a C1 source. These reactions proceed with high atom efficiency via a sequence of dehydrogenation and condensation steps which give rise to selective C-C and C-N bond formations, thereby releasing hydrogen and water. A well-defined hydride Mn(I) PNP pincer complex, recently developed in our laboratory, catalyzes this process in a very efficient way, and a total of 28 different aminomethylated products were synthesized and isolated yields of up to 91%. In a preliminary study, a related Fe(II) PNP pincer complex was shown to catalyze the methylation of 2-naphtol rather than its aminomethylation displaying again the divergent behavior of isoelectronic Mn(I) and Fe(II) PNP pincer systems.
