41605-74-7Relevant academic research and scientific papers
Nickel-Catalyzed Allylic C(sp2)–H Activation: Stereoselective Allyl Isomerization and Regiospecific Allyl Arylation of Allylarenes
Wu, Qiang,Wang, Lanlan,Jin, Rizhe,Kang, Chuanqing,Bian, Zheng,Du, Zhijun,Ma, Xiaoye,Guo, Haiquan,Gao, Lianxun
, p. 5415 - 5422 (2016)
Stereoselective allyl isomerization and regiospecific allyl arylation reactions of allylarenes with a catalytic system comprising nickel(II) with an aryl Grignard reagent were studied. Both reactions are triggered by allylic internal C(sp2)–H activation by in-situ-formed Ni0, which is inserted into the C–H bond at the 2-position of the allyl moiety without a directing group. The isomerization of allylarene to 1-propenylarene favors the E isomer and proceeds with quantitative conversion. The arylation takes place through oxidative cross-coupling of allylarenes with excess Grignard reagent. It occurs regiospecifically at the position of C(sp2)–H activation and represents a new method for the synthesis of 1,1-disubstituted olefins. The results of deuterium labeling experiments reveal an alkenyl/alkyl mechanism involving allylic internal C(sp2)–H activation and multiple intermolecular 1,2-, 1,3-, and 2,3-hydride shifts. These methods represent new approaches to the functionalization of olefins, and the mechanistic investigations could be helpful for the discovery and design of new strategies for olefin functionalization.
Pd-catalyzed ligand-free Suzuki reaction of β-substituted allylic halides with arylboronic acids in water
Dong, Chaonan,Zhang, Lingjuan,Xue, Xiao,Li, Huanrong,Yu, Zhiyong,Tang, Weijun,Xu, Lijin
, p. 11152 - 11158 (2014/03/21)
The catalyst system consisting of Pd(TFA)2 and KOH allows for a wide range of β-substituted allylic halides to react efficiently with various arylboronic acids in neat water under ligand-free conditions, affording the allylated arenes in high yields with broad functional group tolerance and up to 7.4 × 105 TON and 15416 h-1 TOF.
Synthesis of 1,3-diarylpropenes through palladium-catalyzed mizoroki-heck and allyl cross-coupling reactions using hydrazones as ligands
Mino, Takashi,Koizumi, Tomoko,Suzuki, Saori,Hirai, Kiminori,Kajiwara, Kenji,Sakamoto, Masami,Fujita, Tsutomu
supporting information; experimental part, p. 678 - 680 (2012/03/10)
The palladium-catalyzed synthesis of unsymmetrical 1,3-diarylpropenes from allyl esters through a Mizoroki-Heck-type reaction with aryl iodides followed by allyl cross-coupling with a variety of arylboronic acids was developed; the products are obtained in moderate to good yields by using a hydrazone-Pd(OAc) 2 system. The synthesis of unsymmetrical 1,3-diarylpropenes from allyl esters by a Mizoroki-Heck-type reaction followed by allyl cross-coupling with a variety of arylboronic acids was developed; the products were obtained in moderate to good yields by using a hydrazone-Pd(OAc)2 system. Copyright
Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes
Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
, p. 8487 - 8491 (2007/10/03)
cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Heck reaction of disubstituted alkenes such as methyl crotonate, ethyl cinnamate, methyl methacrylate or α-methylstyrene with a variety of aryl halides. In the presence of 1,2-disubstituted alkenes the stereoselectivities of the reactions strongly depend on the substituents of the alkenes. Selectivities up to 97% in favor of E-isomers can be obtained for the addition to methyl crotonate. With the 1,1-disubstituted alkenes methyl methacrylate or α-methylstyrene mixtures of products are obtained.
