1376770-94-3Relevant academic research and scientific papers
A synergistic LUMO lowering strategy using Lewis acid catalysis in water to enable photoredox catalytic, functionalizing C-C cross-coupling of styrenes
Speckmeier, Elisabeth,Fuchs, Patrick J. W.,Zeitler, Kirsten
, p. 7096 - 7103 (2018/09/25)
Easily available α-carbonyl acetates serve as convenient alkyl radical source for an efficient, photocatalytic cross-coupling with a great variety of styrenes. Activation of electronically different α-acetylated acetophenone derivatives could be effected via LUMO lowering catalysis using a superior, synergistic combination of water and (water-compatible) Lewis acids. Deliberate application of fac-Ir(ppy)3 as photocatalyst to enforce an oxidative quenching cycle is crucial to the success of this (umpolung type) transformation. Mechanistic particulars of this dual catalytic coupling reaction have been studied in detail using both Stern-Volmer and cyclic voltammetry experiments. As demonstrated in more than 30 examples, our water-assisted LA/photoredox catalytic activation strategy allows for excess-free, equimolar radical cross-coupling and subsequent formal Markovnikov hydroxylation to versatile 1,4-difunctionalized products in good to excellent yields.
A metal-free transformation of alkynes to carbonyls directed by remote OH group
Chen, Dao-Qian,Guo, Chun-Huan,Zhang, Heng-Rui,Jin, Dong-Po,Li, Xue-Song,Gao, Pin,Wu, Xin-Xing,Liu, Xue-Yuan,Liang, Yong-Min
supporting information, p. 4176 - 4180 (2016/08/02)
A remote OH group-directed metal-free transformation of alkynes to carbonyl compounds has been developed. Using only HOAc and EtOH solvent, this reaction elegantly converts alkynes into valuable ketones by remote hydroxyl group activation. Through comparison and isotope labeling experiments, it was confirmed that the process operates via a hydration reaction involving an acetic acid molecule, instead of a water molecule.
Cleavage of 3-aryl-5,6-dihydro-4H-1,2-oxazines using zinc and aqueous chelating ethers: Efficient methodology for N-O bond cleavage
Kumar, P. Sunil,Rai, K. M. Lokanatha
, p. 440 - 446 (2012/10/07)
A mild and efficient methodology for single pot ring opening of 3-aryl-4H-1,2-oxazines to γ-hydroxy ketones was developed using zinc and aqueous chelating ethers. The ether acts as ligand and co-solvent for the reaction. The ability of zinc ions to form stable complexes with chelating ethers activates the zinc towards reduction. Water is the proton source.
