20780-49-8Relevant articles and documents
Iron Complex Catalyzed Selective C-H Bond Oxidation with Broad Substrate Scope
Jana, Sandipan,Ghosh, Munmun,Ambule, Mayur,Sen Gupta, Sayam
supporting information, p. 746 - 749 (2017/03/01)
The use of a peroxidase-mimicking Fe complex has been reported on the basis of the biuret-modified TAML macrocyclic ligand framework (Fe-bTAML) as a catalyst to perform selective oxidation of unactivated 3° C-H bonds and activated 2° C-H bonds with low catalyst loading (1 mol %) and high product yield (excellent mass balance) under near-neutral conditions and broad substrate scope (18 substrates which includes arenes, heteroaromatics, and polar functional groups). Aliphatic C-H oxidation of 3° and 2° sites of complex substrates was achieved with predictable selectivity using steric, electronic, and stereoelectronic rules that govern site selectivity, which included oxidation of (+)-artemisinin to (+)-10β-hydroxyartemisinin. Mechanistic studies indicate FeV(O) to be the active oxidant during these reactions.
Visible-Light-Promoted Activation of Unactivated C(sp3)-H Bonds and Their Selective Trifluoromethylthiolation
Mukherjee, Satobhisha,Maji, Biplab,Tlahuext-Aca, Adrian,Glorius, Frank
supporting information, p. 16200 - 16203 (2016/12/27)
Selective functionalization of ubiquitous C(sp3)-H bonds using visible light is a highly challenging yet desirable goal in organic synthesis. The development of such processes relies on both rational design and serendipitous discoveries from innovative tools such as screening technologies. Applying a mechanism-based screening strategy, we herein report photoredox-mediated hydrogen atom transfer catalysis for the selective activation of otherwise unactivated C(sp3)-H bonds, followed by their trifluoromethylthiolation, which has high potential as a late-stage functionalization tool. The generality of this method is exhibited through incorporation of the trifluoromethylthio group in a large number of C(sp3)-H bonds with high selectivity without the need for an excess of valuable substrate.
Selective oxidation of unactivated C-H bonds by supramolecular control
Fung, Yat-Sing,Yan, Siu-Cheong,Wong, Man-Kin
experimental part, p. 3122 - 3130 (2012/05/07)
Efficient methods for dioxirane-based selective C-H bond oxidation by supramolecular control in H2O have been developed. With β-cyclodextrin as the supramolecular host, site-selective oxidation of the terminal over the internal tertiary C-H bond of 3,7-dimethyloctyl esters 3a-c was achieved. In addition, β-cyclodextrin selectively enhanced the C-H bond oxidation of cumene in a mixture of cumene and ethyl benzene in H2O. Through 1H NMR studies, the selectivity in C-H bond oxidation could be attributed to the inclusion complex formation between β-cyclodextrin and the substrates. The Royal Society of Chemistry 2012.
