55153-54-3Relevant academic research and scientific papers
Redox-neutral functionalization of α-Csp3-H bonds of secondary cyclic amines: a highly atom-economical strategy forN-arylation/formal cross-dehydrogenative couplings
Husen, Saddam,Jha, Priyankar,Kumar, Ravindra
supporting information, p. 2950 - 2955 (2021/05/05)
An efficient redox-neutral method has been developed for α-Csp3-H functionalization of secondary cyclic aminesviaconcurrentN-arylation/formal cross dehydrogenation coupling (CDC) with sp2-C-H and sp3-C-H bonds of arenes an
Atom Economical Photocatalytic Oxidation of Phenols and Site-Selective Epoxidation Toward Epoxyquinols
Péault, Louis,Planchat, Aurélien,Nun, Pierrick,Le Grognec, Erwan,Coeffard, Vincent
, p. 18192 - 18203 (2021/12/13)
The discovery of a multiple-bond-forming process merging the singlet oxygen-mediated dearomatization of 3,4-disubstitued phenols and diastereo- and regioselective epoxidation is described. This one-pot strategy using a transition metal-free multicatalytic
Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis
Huang, Banruo,He, Ying,Levin, Mark D.,Coelho, Jaime A. S.,Bergman, Robert G.,Toste, F. Dean
supporting information, p. 295 - 301 (2019/11/03)
A chiral phosphoric acid-catalyzed kinetic resolution and desymmetrization of para-quinols operating via oxa-Michael addition was developed and subsequently subjected to mechanistic study. Good to excellent s-factors/enantioselectivities were obtained over a broad range of substrates. Kinetic studies were performed, and DFT studies favor a hydrogen bonding activation mode. The mechanistic studies provide insights to previously reported chiral anion phase transfer reactions involving chiral phosphate catalysts in combination with boronic acids. (Figure presented.).
Site-selective 1,3-double functionalization of arenes using: Para -quinol, C-N, and C-C/C-P three-component coupling
Husen, Saddam,Chauhan, Anil,Kumar, Ravindra
supporting information, p. 1119 - 1124 (2020/03/11)
A catalytic and site-selective approach has been demonstrated for dual functionalization of arenes via cross-coupling reactions of p-quinols with amines and isocyanides/phosphites. The strategy enables the production of a series of 3-amino-benzamides and
Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
Horwitz, Matthew A.,Massolo, Elisabetta,Johnson, Jeffrey S.
supporting information, p. 762 - 767 (2017/06/21)
We report a desymmetrization of cyclohexadienones by intramolecular conjugate addition of a tethered dithiane nucleophile. Mild reaction conditions allow the formation of diversely functionalized fused bicyclic lactones. The products participate in facially selective additions from the convex surface, leading to allylic alcohol derivatives.
Reactions of p-Quinols with Aldehydes and Imines: Stereoselective Access to Polyheterobicyclic and Tricyclic Systems
García-García, Carolina,Redondo, María C.,Ribagorda, María,Carre?o, M. Carmen
, p. 7377 - 7388 (2016/02/20)
Dihydrobenzo[1,3]dioxolanones, tetrahydrobenzo[d]oxazolones and heterotricyclic derivatives have been stereoselectively synthesized from p-quinols upon reaction with aldehydes or benzaldimines under basic catalysis. Reactions occurred in an experimentally
Chiral aryl iodide catalysts for the enantioselective synthesis of para-quinols
Volp, Kelly A.,Harned, Andrew M.
supporting information, p. 3001 - 3003 (2013/05/09)
Molecular modelling of an iodine(iii) phenoxide was used as a starting point in the design of chiral aryl iodide catalysts for stereoselective oxidative dearomatization reactions. Using this approach, catalysts derived from 8-iodotetralone and tartaric ac
Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups
Tello-Aburto, Rodolfo,Kalstabakken, Kyle A.,Volp, Kelly A.,Harned, Andrew M.
, p. 7849 - 7859 (2011/12/04)
The cyclization of 2,5-cyclohexadienones tethered to activated methylene groups was studied. The substitution around the cyclohexadienone ring serves to regioselectively direct these cyclizations based primarily on electronic effects. In the case of brominated substrates, these reactions proceed to give highly unusual electron-deficient tricyclic cyclopropanes. By using a Cinchona alkaloid-based phase-transfer catalyst, prochiral cyclohexadienones can be desymmetrized with moderate stereoselectivity.
Oxidative de-aromatization of para-alkyl phenols into para-peroxyquinols and para-quinols mediated by oxone as a source of singlet oxygen
Carreno, M. Carmen,Gonzalez-Lopez, Marcos,Urbano, Antonio
, p. 2737 - 2741 (2007/10/03)
(Chemical Equation Presented) Easy does it: Easily handled and environmentally safe oxone generates singlet oxygen which effects the simple and selective oxidative de-aromatization of para-alkyl phenols 1 into para-peroxyquinols 2 under very mild conditions with good to excellent yields. A one-pot access to para-quinols 3 from 1 is also possible after treatment of the crude reaction mixture with sodium thiosulfate.
A Simple and Efficient Procedure for the Preparation of p-Quinols by Hypervalent Iodine Oxidation of Phenols and Phenol Tripropylsilyl Ethers
McKillop, Alexander,McLaren, Lee,Taylor, Richard J. K.
, p. 2047 - 2048 (2007/10/02)
Oxidation of para-substituted phenols with benzene (BTIB) in aqueous acetonitrile at 0 deg C gives p-quinols in moderate to good yields; higher yields are obtained when tripropylsilyl ethers of phenols are used.
