5958-02-1Relevant articles and documents
5,6- and 6,6-Membered Palladium(II) Pincer Complexes Based on Functionalized Carboxamides with Ancillary Sulfur and Nitrogen Donors
Churusova, Svetlana G.,Aleksanyan, Diana V.,Vasil'ev, Andrei A.,Nelyubina, Yulia V.,Novikov, Valentin V.,Pavlov, Alexander A.,Denisov, Gleb L.,Klemenkova, Zinaida S.,Kozlov, Vladimir A.
, p. 5271 - 5280 (2016)
New multidentate ligands have been synthesized by the condensation of 2-(methylsulfanyl)benzoyl chloride with a range of amines bearing ancillary N or S donors. In reactions with PdCl2(NCPh)2, the ligands smoothly underwent direct cyclopalladation to give pincer complexes with 5,6- or 6,6-membered fused metallocycles. The oxidation of the sulfide ligands with H2O2afforded the corresponding sulfoxide derivatives, which readily formed analogous pincer complexes with the PdIIions. The realization of κ3-S,N,X coordination (X = N or S) was confirmed by multinuclear NMR and IR spectroscopic data and, in some cases, X-ray crystallography. An unusual dynamic behavior of the 6,6-membered S,N,S complex with an organophosphorus ligand was additionally studied by the ROESY technique. All of the palladocycles obtained were tested as precatalysts for the Suzuki cross-coupling of aryl bromides with arylboronic acids, which allowed us to evaluate the main structure–activity relationships.
Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls
Blakemore, David C.,Cervantes-Reyes, Alejandro,Chinigo, Gary M.,Smith, Aaron C.,Szostak, Michal
supporting information, p. 1678 - 1683 (2022/03/14)
Heteroaromatic biaryls are core scaffolds found in a plethora of pharmaceuticals; however, their direct synthesis by the Suzuki cross-coupling is limited to heteroaromatic halide starting materials. Here, we report a direct synthesis of diverse nitrogen-containing heteroaromatic biaryls by Pd-catalyzed decarbonylative Suzuki cross-coupling of widely available heterocyclic carboxylic acids with arylboronic acids. The practical and modular nature of this cross-coupling enabled the straightforward preparation of >45 heterobiaryl products using pyridines, pyrimidines, pyrazines, and quinolines in excellent yields. We anticipate that the modular nature of this protocol will find broad application in medicinal chemistry and drug discovery research.
A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents
He, Xiao-Yun
, p. 823 - 832 (2021/07/19)
Pd(OAc)2/1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxy-piperidine was demonstrated to effectively catalyze cross-coupling of aryl fluoride and aryl(alkyl) titanium reagent. Both electron-deficient and electron-rich aryl fluoride can react effectively with nucleophile and provide extensive functional groups tolerance. 2-Arylated product was realized by selective activation of the C–F bond. Graphic abstract: [Figure not available: see fulltext.].