590400-91-2Relevant academic research and scientific papers
Iron-Catalysed Remote C(sp3)?H Azidation of O-Acyl Oximes and N-Acyloxy Imidates Enabled by 1,5-Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ-Azido Ketones and β-Azido Alcohols
Torres-Ochoa, Rubén O.,Leclair, Alexandre,Wang, Qian,Zhu, Jieping
supporting information, p. 9477 - 9484 (2019/05/21)
In the presence of a catalytic amount of iron(III) acetylacetonate [Fe(acac)3], the reaction of structurally diverse ketoxime esters with trimethylsilyl azide (TMSN3) afforded γ-azido ketones in good to excellent yields. This unprecedented distal γ-C(sp3)?H bond azidation reaction went through a sequence of reductive generation of an iminyl radical, 1,5-hydrogen atom transfer (1,5-HAT) and iron-mediated redox azido transfer to the translocated carbon radical. TMSN3 served not only as a nitrogen source to functionalise the unactivated C(sp3)?H bond, but also as a reductant to generate the catalytically active FeII species in situ. Based on the same principle, a novel β-C(sp3)?H functionalisation of alcohols via N-acyloxy imidates was subsequently realised, leading, after hydrolysis of the resulting ester, to β-azido alcohols, which are important building blocks in organic and medicinal chemistry.
Transition metals catalyzed C-C and C-O bonds formation: Facile synthesis of flavans and benzoxepines
Ramulu, B. Venkat,Mahendar,Krishna,Reddy, A. Gopi Krishna,Suchand,Satyanarayana
, p. 8305 - 8315 (2013/09/02)
A simple and practical method has been developed based on intermolecular [Pd]-catalyzed C-C and an intramolecular [Cu]-catalyzed C-O bond formations for the synthesis of flavans and benzoxepines. Interestingly, the method is amenable for the synthesis of
Asymmetric palladium-catalyzed intramolecular α-arylation of aldehydes
Garcia-Fortanet, Jorge,Buchwald, Stephen L.
supporting information; experimental part, p. 8108 - 8111 (2009/04/13)
(Chemical Equation Presented) Phoxy ligand: The first catalytic method for the asymmetric palladium-catalyzed intramolecular α-arylation of α-branched aldehydes was developed (see scheme). This process is distinguished by the high yields and enantioselectivities that can be obtained, making this protocol a useful synthetic tool for further applications.
Synthesis of 2-substituted 1-benzyl-2,3,4,5-tetrahydro-1-benzazepines by palladium catalysis. Observation of a competitive β-hydride elimination pathway
Qadir, Maryiam,Priestley, Rachael E.,Rising, Thomas W. D. F.,Gelbrich, Thomas,Coles, Simon J.,Hursthouse, Michael B.,Sheldrake, Peter W.,Whittall, Neil,Hii
, p. 3675 - 3678 (2007/10/03)
A synthetic route to 1-benzyl-tetrahydro-1-benzazepine is reported, which also permits access to analogous structures with alkyl and aryl substituents at position-2 of the aliphatic ring. Palladium catalysis is utilized in two of the three steps, construc
