52107-61-6Relevant 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.
Palladium-catalyzed tandem dimerization and cyclization of acetylenic ketones: A convenient method for 3,3′-bifurans using PdCl2(PPh3)2
Jeevanandam,Narkunan,Ling
, p. 6014 - 6020 (2007/10/03)
Alkynones undergo tandem dimerization and cyclization in the presence of PdCl2(PPh3)2 and triethylamine in tetrahydrofuran at room temperature to give 3,3′-bifurans predominantly. Other palladium catalysts while under similar conditions, by rearrangement, lead to 2,5-disubstituted furans. This distinguished property of PdCl2(PPh3)2 has been attributed to the involvement of hydridopalladium halide. This method provides a simpler route to a variety of furans and a regioselective synthesis of polysubstituted 3,3′-bifurans using easily accessible acetylenic ketones.
A novel palladium-catalyzed tandem dimerization and cyclization of acetylenic ketones. A convenient method for 3,3'-bifurans
Jeevanandam, Arumugasamy,Narkunan, Kesavaram,Cartwright, Charles,Ling, Yong-Chien
, p. 4841 - 4844 (2007/10/03)
Alkynones undergo rearrangement in the presence of Pd(PPh3)4 and triethylamine in tetrahydrofuran at room temperature to give 2,5-substituted furans, but under similar conditions PdCl2(PPh3)2, by a tandem dimerization and cyclization, gives 3,3'-bifurans predominantly.
Cathodic Reduction of 1,2-Dibenzoylchloroethane. Formation of Cyclic Dimolecular Products
Barba, Fructuoso,Fuente, Jose Luis de la
, p. 7685 - 7687 (2007/10/02)
The electrochemical reduction of 1,2-dibenzoylchloroethane in aprotic medium (DMF-LiClO4) on mercury cathode gives four dimeric products.Two of them correspond to cyclic structures, 1-phenyl-c-2,t-3,c-4-tribenzoyl-r-1-cyclopentanol (41-43percent) and 1-phenyl-c-2,c-3,t-4-tribenzoyl-r-1-cyclopentanol (16-18percent), and the other two were identified as the racemic and meso 1,6-diphenyl-3,4-dibenzoyl-1,6-butanediones (24-26 and 8-10percent, respectively).The dehydration of these products leads to the formation of furans, bisfurans, or cyclopentenes depending on the experimental conditions.
