39858-88-3Relevant academic research and scientific papers
Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides
Fu, Yue,Liu, Fang-Jie,Liu, Peng,Tang, Jian-Tao,Toste, F. Dean,Wu, Ting-Feng,Ye, Baihua,Zhang, Yue-Jiao
supporting information, p. 1963 - 1974 (2021/07/07)
Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.
Csp2-Br bond activation of Br-pyridine by neophylpalladacycle: Formation of binuclear seven-membered palladacycle and bipyridine species
Nicasio-Collazo, Juan,Wrobel, Katarzyna,Wrobel, Kazimierz,Serrano, Oracio
supporting information, p. 8729 - 8733 (2017/08/29)
In this work, the synthesis and reactivity of seven-membered palladacycles are described, and a novel bi-pyridine synthesis in a catalytic pathway is reported. Neophyl-palladacycle(i) reacts with an excess of 2-Br-pyridine, giving the desired new binuclear seven-membered palladacycle (1) and unexpectedly, a bipyridine complex, [Pd(BiPy)Br2]. ESI-HRMS experiments show that fragmentation of the Pd-Br bond in 1 can take place producing unusual two coordinated Pd(ii) molecular ions, [Pd(NeoPyR)]+.
Tetrabutylammonium 2-pyridyltriolborate salts for Suzuki-Miyaura cross-coupling reactions with aryl chlorides
Sakashita, Shohei,Takizawa, Miho,Sugai, Juugaku,Ito, Hajime,Yamamoto, Yasunori
supporting information, p. 4308 - 4311 (2013/09/24)
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corresponding lithium salts. The coupling reactions with aryl chlorides progressed in the presence of PdCl2dcpp (3 mol %) and CuI/MeNHCH 2CH2OH (20 mol %) in anhydrous DMF without bases.
Syntheses of Hydroxylated Bipyridines, III. - Synthesis of Unsymmetrically and Symmetrically Structured Dihydroxybipyridines
Dehmlow, Eckehard V.,Sleegers, Arthur
, p. 953 - 960 (2007/10/02)
Fifteen symmetrical and asymmetrical dimethoxybipyridines and the pertinent diols are prepared and characterized.Reductive cross coupling of halopyridines with Ni(0) may result in complex mixtures.The same is true for an alternative reaction of (trimethylstannyl)pyridines with halopyridines in the presence of Pd(0).UV, 1H-, and 13C-NMR spectra of the bipyridine derivatives are tabulated.Key Words: Bipyridinediols / Pyridines / Stannylpyridines
ACTIVATION OF REDUCING AGENTS. SODIUM HYDRIDE CONTAINING COMPLEX REDUCING AGENTS 23. SYMMETRICAL COUPLING OF NITROGEN-CONTAINING HETEROCYCLIC HALIDES
Vanderesse, R.,Lourak, M.,Fort, Y.,Caubere, P.
, p. 5483 - 5486 (2007/10/02)
The preparation of NiCRA (NaH-tBuONa-Ni(OAc)2) in the presence of PPh3 leads to a reagent (termed NiCRA-PPh3) which is shown to be one of the most efficient Ni containing reagents reported so far for the homocoupling of heteroaromatic halides.
