24764-60-1Relevant academic research and scientific papers
Palladium-catalyzed cyclocoupling of 2-halobiaryls with isocyanides via the cleavage of carbon-hydrogen bonds
Tobisu, Mamoru,Imoto, Shinya,Ito, Sana,Chatani, Naoto
supporting information; body text, p. 4835 - 4840 (2010/10/04)
(Figure Presented) To demonstrate the utility of isocyanides in catalytic C-H bond functionalization reactions, a palladium-catalyzed cyclocoupling reaction of 2-halobiaryls with isocyanides was developed. The reaction afforded an array of fluorenone imine derivatives via the cleavage of a C-H bond at the 2′-position of 2-halobiaryls. The use of 2,6-disubstituted phenyl isocyanide was crucial for this catalytic cyclocoupling reaction to proceed. The reaction was applicable to heterocyclic and vinylic substrates, allowing the construction of a wide range of ring system. The large kinetic isotope effect observed (kH/kD = 5.3) indicates that C-H bond activation was the turnover-limiting step in this catalysis.
