63615-92-9Relevant articles and documents
Buchwald-Hartwig Amination of Coordinating Heterocycles Enabled by Large-but-Flexible Pd-BIAN-NHC Catalysts**
Li, Dong-Hui,Lan, Xiao-Bing,Song, A-Xiang,Rahman, Md. Mahbubur,Xu, Chang,Huang, Fei-Dong,Szostak, Roman,Szostak, Michal,Liu, Feng-Shou
supporting information, (2021/12/06)
A new class of large-but-flexible Pd-BIAN-NHC catalysts (BIAN=acenaphthoimidazolylidene, NHC=N-heterocyclic carbene) has been rationally designed to enable the challenging Buchwald-Hartwig amination of coordinating heterocycles. This robust class of BIAN-NHC catalysts permits cross-coupling under practical aerobic conditions of a variety of heterocycles with aryl, alkyl, and heteroarylamines, including historically challenging oxazoles and thiazoles as well as electron-deficient heterocycles containing multiple heteroatoms with BIAN-INon (N,N′-bis(2,6-di(4-heptyl)phenyl)-7H-acenaphtho[1,2-d]imidazol-8-ylidene) as the most effective ligand. Studies on the ligand structure and electronic properties of the carbene center are reported. The study should facilitate the discovery of even more active catalyst systems based on the unique BIAN-NHC scaffold.
Generating Active L-Pd(0) via Neutral or Cationic π-Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure-Activity Studies in Challenging Cross-Coupling Reactions
Deangelis,Gildner, Peter G.,Chow, Ruishan,Colacot, Thomas J.
, p. 6794 - 6813 (2015/10/06)
Two new classes of highly active yet air- and moisture-stable π-R-allylpalladium complexes containing bulky biaryl- and bipyrazolylphosphines with extremely broad ligand scope have been developed. Neutral π-allylpalladium complexes incorporated a range of biaryl/bipyrazolylphosphine ligands, while extremely bulky ligands were accommodated by a cationic scaffold. These complexes are easily activated under mild conditions and are efficient for a wide array of challenging C-C and C-X (X = heteroatom) cross-coupling reactions. Their high activity is correlated to their facile activation to a 12-electron-based L-Pd(0) catalyst under commonly employed conditions for cross-coupling reactions, noninhibitory byproduct release upon activation, and suppression of the off-cycle pathway to form dinuclear (μ-allyl)(μ-Cl)Pd2(L)2 species, supported by structural (single crystal X-ray) and kinetic studies. A broad scope of C-C and C-X coupling reactions with low catalyst loadings and short reaction times highlight the versatility and practicality of these catalysts in organic synthesis.
Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters
Schnürch, Michael,Waldner, Birgit,Hilber, Karlheinz,Mihovilovic, Marko D.
experimental part, p. 2149 - 2154 (2011/04/24)
A series of N-arylthiazole-2-amines was prepared and their biological activity for the promotion of skeletal muscle cell differentiation was investigated, a process of significant importance in muscle regeneration. A versatile new synthetic route towards
