109660-12-0Relevant 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.
, 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.
Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands
Ghorai, Debasish,Müller, Valentin,Keil, Helena,Stalke, Dietmar,Zanoni, Giuseppe,Tkachenko, Boryslav A.,Schreiner, Peter R.,Ackermann, Lutz
supporting information, p. 3137 - 3141 (2017/09/06)
C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides
Natural Kaolinitic clay catalyzed conversion of nitriles to 2-oxazolines
Jnaneshwara,Deshpande,Lalithambika,Ravindranathan,Bedekar
, p. 459 - 462 (2007/10/03)
Natural Kaolinitic clay has been found effective as catalyst in the conversion of aromatic and aliphatic nilriles with 1,2-aminoalcohol to 2-oxazolines (56-96%, yield).
Palladium-Catalyzed Coupling of Oxazol-2-yl and 2-Oxazolin-2-yltrimethylstannanes with Aromatic Halides. A New Entry to 2-Aryl and 2-Heteroaryl Oxazoles and Oxazolines
Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola
, p. 693 - 696 (2007/10/02)
4-Methyloxazole and 4,4-dimethyl-2-oxazoline were treated with n-butyllithium and trimethyltin chloride to give the corresponding 2-trimethylstannyl derivatives which in the presence of tetrakis(triphenylphosphine)palladium(0) as a catalyst undergo cross-
MASKED MULTIFUNCTIONALIZATION OF AROMATICS BY PALLADIUM-CATALYZED HALOGEN-OXAZOLINE EXCHANGE
Dondoni, Alessandro,Fogagnolo, Marco,Fantin, Giancarlo,Medici, Alessandro,Pedrini, Paola
, p. 5269 - 5270 (2007/10/02)
The (Ph3P)4Pd-catalyzed cross-coupling of aryl and heteroaryl halides with 2-(trimethylstannyl)-4,4-dimethyl-2-oxazoline 3 affords aromatic 2-oxazolines 6 in very high yields.
