226387-11-7Relevant articles and documents
Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids**
Deng, Ruohan,Engle, Keary M.,Fu, Yue,Gao, Yang,Li, Zi-Qi,Liu, Peng,Tran, Van T.
supporting information, p. 23306 - 23312 (2020/10/19)
A nickel-catalyzed regiodivergent hydroarylation and hydroalkenylation of unactivated alkenyl carboxylic acids is reported, whereby the ligand environment around the metal center dictates the regiochemical outcome. Markovnikov hydrofunctionalization products are obtained under mild ligand-free conditions, with up to 99 % yield and >20:1 selectivity. Alternatively, anti-Markovnikov products can be accessed with a novel 4,4-disubstituted Pyrox ligand in excellent yield and >20:1 selectivity. Both electronic and steric effects on the ligand contribute to the high yield and selectivity. Mechanistic studies suggest a change in the turnover-limiting and selectivity-determining step induced by the optimal ligand. DFT calculations reveal that in the anti-Markovnikov pathway, repulsion between the ligand and the alkyl group is minimized (by virtue of it being 1° versus 2°) in the rate- and regioselectivity-determining transmetalation transition state.
Efficacious and rapid metal- and solvent-free synthesis of enantiopure oxazolines
Hassani, Rym,Requet, Alexandre,Marque, Sylvain,Gaucher, Anne,Prim, Damien,Kacem, Yakdhane,Hassine, Bchir Ben
, p. 1275 - 1279 (2015/01/08)
A rapid and efficient synthesis of oxazolines was performed starting from various nitriles using microwave irradiation combined to metal- and solvent-free conditions to afford high to quantitative yields of the targeted heterocycles.
Palladium(II)-catalyzed enantioselective aerobic dialkoxylation of 2-propenyl phenols: A pronounced effect of copper additives on enantioselectivity
Zhang, Yang,Sigman, Matthew S.
, p. 3076 - 3077 (2008/04/18)
A direct O2-coupled Pd(II)-catalyzed enantioselective dialkoxylation of 2-propenylphenols has been developed by utilizing chiral quinoline oxazoline ligands. A detrimental effect of added copper salts on enantioselectivity was observed which is attributed to the displacement of the chiral ligand off of Pd(II). Copyright