28861-25-8Relevant articles and documents
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.
Preparation, Properties and Crystal Structures of New Nickel(II) Complexes of 1,2-Asymmetrically Substituted Dithiolenes for Third-order Non-linear Optical Applications
Hill, Callum A. S.,Charlton, Adam,Underhill, Allan E.,Malik, K. M. Abdul,Hursthouse, Michael B.,et al.
, p. 587 - 594 (2007/10/02)
Three new nickel(II) complexes of 1-alkyl-2-phenyl asymmetrically substituted dithiolenes 1=CR2S)2> (R1 = Ph; R2 = n-Bu, cyclopentylmethyl or 4-pentylcyclohexyl) have been prepared and their electrochemic