0000000000082915
AUTHOR
Cristian Mollar
ChemInform Abstract: Switchable Palladium-Catalyst Reaction of Bromomethyl Sulfoxides, CO, and N-Nucleophiles: Aminocarbonylation at Csp3versus Oxidative Carbonylation of Amines.
Pd2(dba)3/ Xantphos-catalyzed coupling of the sulfoxides (I) and (V) with amines and carbon monoxide allows a new and efficient access to amides of type (IV) and (VI).
Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Halomethyl Oxime Ethers and Site-Selective Cross-Coupling of Dihalo Derivatives
The Pd-catalyzed cross-coupling reaction of chloromethyl oxime ethers with a wide range of aryl-, heteroaryl-, and vinylboronic acids proceeds with good yields.
First Synthesis of β-Keto Sulfoxides by a Palladium-Catalyzed Carbonylative Suzuki Reaction
[reaction: see text] An unprecedented palladium-catalyzed three-component cross-coupling reaction between alpha-bromo sulfoxide, carbon monoxide, and aromatic boronic acids provides a new and efficient approach to the synthesis of beta-ketosulfoxides. The reaction takes place under mild conditions with a wide range of variously substituted aryl and heteroaryl boronic acids. The carbonylative cross-coupling reaction is strongly favored over competing direct cross-coupling and homocoupling processes, except with boronic acids carrying strong electron-withdrawing substituents.
Switchable palladium-catalyst reaction of bromomethyl sulfoxides, CO, and N-nucleophiles: aminocarbonylation at Csp3 versus oxidative carbonylation of amines.
The palladium-catalyzed reaction of α-bromomethyl sulfoxides, carbon monoxide, and N-nucleophiles follows different reaction pathways according to the catalytic system and the reaction conditions. The Pd-xantphos catalyst affords high yields of α-sulfinyl amides by an aminocarbonylation process and is the first example of this type of transformation for a nonbenzylic sp(3)-hybridized carbon. On the other hand, the oxidative carbonylation of amines occurs with α-bromomethyl sulfoxides, carbon monoxide, and catalytic Pd(PPh(3))(4) under aerobic conditions, yielding ureas and oxalamides from either primary or secondary amines. The reaction with ambident nucleophiles such as amino alcohols was …
Competitive and Selective Csp3Br versus Csp2Br Bond Activation in Palladium-Catalysed Suzuki Cross-Coupling: An Experimental and Theoretical Study of the Role of Phosphine Ligands
Phosphine ligands have been demonstrated to have an effect on reactivity and selectivity in the competitive intramolecular palladium-catalysed Suzuki-Miyaura coupling of dibromo sulfoxide 1a possessing two different hybridised electrophilic carbons. It was found that the bromine bond to the sp(3)-hybridised carbon is selectively replaced in the presence of unhindered phosphines such as PPh(3) or xantphos. The use of hindered phosphine ligands such as P(o-tol)(3) and P(1-naphthyl)(3) reversed the selectivity, conducting the cross-coupling at the Csp(2)-Br. Identical trends were observed in external competition experiments carried out with bromomethyl sulfoxide and different substituted bromo…
ChemInform Abstract: Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Halomethyl Oxime Ethers and Site-Selective Cross-Coupling of Dihalo Derivatives.
The Pd-catalyzed cross-coupling reaction of chloromethyl oxime ethers with a wide range of aryl-, heteroaryl-, and vinylboronic acids proceeds with good yields.
CCDC 965392: Experimental Crystal Structure Determination
Related Article: Cristian Mollar , Carmen Ramirez de Arellano , Mercedes Medio-Simón , and Gregorio Asensio|2012|J.Org.Chem.|77|9693|doi:10.1021/jo301778n
CCDC 965391: Experimental Crystal Structure Determination
Related Article: Cristian Mollar , Carmen Ramirez de Arellano , Mercedes Medio-Simón , and Gregorio Asensio|2012|J.Org.Chem.|77|9693|doi:10.1021/jo301778n