61259-78-7Relevant articles and documents
Synthesis of Di- and Triarylmethanes through Palladium-Catalyzed Reductive Coupling of N -Tosylhydrazones and Aryl Bromides
Xia, Yamu,Hu, Fangdong,Xia, Ying,Liu, Zhenxing,Ye, Fei,Zhang, Yan,Wang, Jianbo
, p. 1073 - 1086 (2017/02/24)
A palladium-catalyzed reductive coupling between N-tosylhydrazones and aryl bromides has been developed. The reaction provides an efficient method for the synthesis of diarylmethanes and triarylmethanes via the formation of C(sp2)-C(sp3) single bonds. This new methodology for the synthesis of diarylmethanes and triarylmethanes is featured by the ready availability of the starting materials, mild reaction conditions, and the tolerance of wide range of functional groups. The reaction follows a pathway including palladium carbene formation, migratory insertion, and reduction of the alkylpalladium(II) intermediate.
PREDOMINANT O-ALKYLATION IN THE ATTACK OF FREE BENZYL CATION ON 2,6-DIMETHYLANISOLE
Angelini, Giancarlo,Sparapani, Cinzia,Speranza, Maurizio
, p. 479 - 484 (2007/10/02)
Labelled benzyl cation from the decay of side-chain multitritiated toluene has been allowed to react with 2,6-dimethylanisole in n-hexane, nitromethane, and diethyl ether solutions at room temperature The nuclear-decay formed (nucleogenic) benzyl cation displays high selectivity toward the n-type centre of the nucleophiles present, leading to predominant formation of benzyl 2,6-dimethylphenyl ether in n-hexane and nitromethane, via the O-benzylated oxonium intermediate.In n-hexane, the oxonium intermediate undergoes partial isomerization, yielding the corresponding ring-substituted products (0.5 meta/para = 1.3).A mechanism involving a tight sandwich ? complex is proposed to account for the solvent effect on product distribution.The mechanistic features of the benzylation process, deduced from the decay experiments, are discussed and compared with those of related gas-phase and conventional Friedel-Crafts data.
