54245-99-7Relevant academic research and scientific papers
Oxidative Coupling of N-Methoxyamides and Related Compounds toward Aromatic Hydrocarbons by Designer μ-Oxo Hypervalent Iodine Catalyst
Dohi, Toshifumi,Sasa, Hirotaka,Dochi, Mio,Yasui, Chihiro,Kita, Yasuyuki
, p. 1185 - 1195 (2019/02/26)
Oxidative coupling strategies that can directly convert the C-H group for chemical transformations are, in theory, ideal synthetic methods to reduce the number of synthetic steps and byproduct generation. Hypervalent iodine reagents have now become one of the most promising tools in developing oxidative couplings due to their unique reactivities that are replacing metal oxidants. As part of our continuous development of oxidative coupling reactions, we describe in this report highly efficient μ-oxo hypervalent iodine catalysts for the direct oxidative coupling of N -methoxyamides and related compounds with aromatic hydrocarbons. The excellent TONs, up to over 100 times, with a best catalyst loading of 0.5 mol% were determined for the oxidative C-H/N-H coupling method, which can provide the most straightforward route to obtaining these unique arylamide compounds.
An Improved Catalyst for Iodine(I/III)-Catalysed Intermolecular C H Amination
Lucchetti, Nicola,Scalone, Michelangelo,Fantasia, Serena,Mu?iz, Kilian
, p. 2093 - 2099 (2016/07/16)
1,2-Diiodobenzene is presented as an efficient catalyst precursor for the intermolecular amination of arenes under homogeneous conditions. N-Troc- and N-phthalimido-substituted methoxyamines serve as suitable nitrogen sources providing the corresponding aniline derivatives in up to 99% yield and with up to 66:1 regioselectivity. Key for this successful C N coupling protocol is the strained μ-oxo-bridged conformation of the bisiodine(III) catalyst, which induces unparalleled high reactivity. (Figure presented.) .
Cesium Carbonate Promoted Direct Arylation of Hydroxylamines and Oximes with Diaryliodonium Salts
Yang, Yang,Wu, Xunshen,Han, Jianwei,Mao, Song,Qian, Xiaofei,Wang, Limin
supporting information, p. 6854 - 6857 (2016/02/19)
A transition-metal-free approach for the arylation of hydroxylamines and oximes with diaryliodonium salts was developed. The reaction proceeded smoothly at room temperature in the presence of cesium carbonate. As a result, a wide range of N- and O-arylate
Organocatalytic, oxidative, intermolecular amination and hydrazination of simple arenes at ambient temperature
Samanta, Rajarshi,Antonchick, Andrey P.,Bauer, Jonathan O.,Strohmann, Carsten
supporting information, p. 5518 - 5521,4 (2012/12/12)
New atom-economical, environmental friendly, direct oxidative intermolecular processes of amination and hydrazination of nonprefunctionalized arenes were developed. The products were formed in a good regioselective manner under organocatalytic conditions
Copper-catalyzed cross-coupling of O -alkyl hydroxamates with aryl iodides
Kukosha, Tatyana,Trufilkina, Nadezhda,Belyakov, Sergey,Katkevics, Martins
experimental part, p. 2413 - 2423 (2012/09/07)
N-Aryl-O-alkylhydroxamic acid derivatives were prepared by copper-catalyzed cross-coupling of hydroxamates with aryl iodides. The reaction conditions are compatible with standard hydroxy-protecting groups on the hydroxylamine moiety and are applicable to
One-pot formation of C-C and C-N bonds through palladium-catalyzed dual C-H activation: Synthesis of phenanthridinones
Wang, Guan-Wu,Yuan, Ting-Ting,Li, Dan-Dan
supporting information; experimental part, p. 1380 - 1383 (2011/04/18)
Two cycles in one pot! The synthesis of biologically important phenanthridinones has been achieved by the one-pot formation of C-C and C-N bonds through a palladium-catalyzed dual C-H activation, which involves four bond ruptures and two bond formations (see scheme). The conversion of phenanthridinones into natural product like derivatives further demonstrates the utility of this synthetic achievement.
CYCLIZATION WITH NITRENIUM IONS GENERATED FROM N-METHOXY- OR N-ALLYLOXY-N-CHLOROAMIDES WITH ANHYDROUS ZINC ACETATE. SYNTHESIS OF N-HYDROXY- AND N-METHOXYNITROGEN HETEROCYCLIC COMPOUNDS
Kikugawa, Yasuo,Shimada, Masahiro,Matsumoto, Kazuhiro
, p. 293 - 302 (2007/10/02)
Electrophilic intramolecular aromatic substitution with an N-methoxy- or an N-allyloxyacylnitrenium ion, generated by treatment of an N-methoxy- or an N-allyloxy-N-chloroamide with anhydrous zinc acetate in nitromethane, leads to formation of a nitrogen h
Anionic [3,3]-sigmatropic rearrangement of N-phenyl-O-acylhydroxylamines to o-aminophenylcetic acids
Endo, Yasuyuki,Hizatate, Shoji,Shudo, Koichi
, p. 2803 - 2806 (2007/10/02)
N-Phenyl-O-acylhydroxylamines rearrange under basic conditions to afford o-aminophenylacetic acids. The rearrangement can be rationalized in terms of [3,3]-sigmatropic shifts of an enolized N-phenyl-O-acylhydroxyl-amine.
Electrophilic Aromatic Substitution with N-Methoxy-N-acylnitrenium Ions Generated from N-Chloro-N-methoxyamides: Syntheses of Nitrogen Heterocyclic Compounds Bearing a N-Methoxyamide Group
Kawase, Masami,Kitamura, Takahiro,Kikugawa, Yasuo
, p. 3394 - 3403 (2007/10/02)
N-Methoxy-N-acylnitrenium ions (II), generated by treatment of N-chloro-N-methoxyamides with silver carbonate in trifluoroacetic acid, react with arenes to give N-aryl-N-methoxyamides in good yields.In the case of the intramolecular cyclization of N-chloro-N-methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups.Nitrenium ions II can primarily attack three positions (C-1, C-2, and C-6) of a phenyl ring.Normally II attack C-6.On the other hand, when the ortho position was occupied with a substituent group, II attacked both C-2 and C-6, in the former case followed by a 1,2-substituent migration, which was proved by a deuterium labeling experiment.Especially, when a methoxy group is substituted on ortho or para position, II attack C-1 due to the effect of the electron-releasing methoxy group to give spiro dienone compounds 39.A general discussion of the utility and mechanistic details of these reactions is presented.
N-ALKOXY-N-ACYLNITRENIUM IONS IN INTRAMOLECULAR AROMATIC ADDITION REACTIONS
Glover, Stephen A.,Goosen, Andre,McCleland, Cedric W.,Schoonraad, Johan L.
, p. 2577 - 2592 (2007/10/02)
N-alkoxy-N-acylnitrenium ions are generated by treatment of N-alkoxy-N-chloroamides with silver ions in ethereal solvents.These intermediates readily cyclise onto aromatic nuclei on alkoxy side-chains to give benzoxazines and benzoxazepines and on the acyl side-chains to give γ, δ and ε benzolactams.Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side-chain aromatic rings.The yields and regioselectivities of these reactions have been ascribed to different transition structures for cyclisation onto the acyl and alkoxy side-chains which involve respectively an exocyclic and endocyclic N-O ?-bond.Evidence for this exeptionally high ?-bond character has been obtained from MNDO calculations which predict a ?-bond order of 0.9 and a rotational barrier of 29.7 kcalmol-1
