54246-01-4Relevant 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.
Organocatalytic, oxidative, intermolecular amination and hydrazination of simple arenes at ambient temperature
Samanta, Rajarshi,Antonchick, Andrey P.,Bauer, Jonathan O.,Strohmann, Carsten
, 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
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
