67330-67-0Relevant academic research and scientific papers
Mild negishi cross-coupling reactions catalyzed by acenaphthoimidazolylidene palladium complexes at low catalyst loadings
Liu, Zelong,Dong, Ningning,Xu, Mizhi,Sun, Zheming,Tu, Tao
, p. 7436 - 7444 (2013/09/02)
Considering that the strong σ-donor property of ylidenes derived from π-extended imidazolium salts is conducive to increasing the catalytic activity of the resulting palladium N-heterocyclic carbene complexes, robust acenaphthoimidazol-ylidene palladium complexes 3a-c with varying bulky substituted groups were prepared from the corresponding acenaphthoimidazolium chlorides by heating with PdCl2 and K2CO3 in neat 3-chloropyridine in satisfactory yields. Even at a catalyst loading as low as 0.25 mol %, complex 3a exhibited extremely high catalytic activity toward Negishi cross-coupling of alkylzinc reagents with a wide range of (hetero)aryl halides under mild reaction conditions within 30 min. Besides a great number of bromoarenes, various less expensive and inactive (hetero)aryl chlorides were coupled successfully with the alkyl- and arylzinc reagents, in which active functional groups (such as -NH2) were well tolerated even in one-pot dicoupling transformations without protection. In addition, in the case of coupling with secondary alkylzinc reagents, undesired β-hydride elimination leading to isomerized linear products was efficaciously suppressed. The catalyst system also displayed superiority in the construction of heterobiaryls through the coupling of heteroarylzinc reagents and heterocylic chloroarenes which were hardly accessible from the corresponding organoboron reagents by Suzuki-coupling reactions. Therefore, the protocol described in this paper represents a mild, general, and scalable approach to access various structurally intriguing and functionalized (hetero)aryls.
Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent
Alimsiz, Seluk,Organ, Michael G.
supporting information; experimental part, p. 5181 - 5183 (2011/06/09)
Pd-PEPPSI-IPent has proven to be an excellent catalyst for the Negishi cross-coupling reaction of secondary alkylzinc reagents with a wide variety of aryl/heteroaryl halides. Importantly, β-hydride elimination/migratory insertion of the organometallic leading to the production of isomeric coupling products has been significantly reduced using the highly-hindered Ipent ligand.
Design of arylimine postmetallocene catalytic systems for olefin polymerization: I. Synthesis of substituted 2-cycloalkyl- and 2,6-dicycloalkylanilines
Oleinik,Oleinik,Abdrakhmanov,Ivanchev,Tolstikov
, p. 1423 - 1427 (2007/10/03)
A convenient synthetic approach to substituted 2-cycloalkyl- and 2,6-dicycloalkylanilines, involving catalytic hydrogenation on Raney nickel in methanol of readily available o-cycloalkenylanilines prepared by reaction of cyclic alkyl halides with anilines
