53183-60-1Relevant academic research and scientific papers
Palladium(II)-catalyzed cross-coupling of diazo compounds and isocyanides to access ketenimines
Bi, Xihe,Liu, Zhaohong,Cao, Shanshan,Wu, Jiayi,Zanoni, Giuseppe,Sivaguru, Paramasivam
, p. 12881 - 12887 (2020)
Diazo compounds and isocyanides are reactive functionalities and valuable building blocks commonly utilized in organic synthesis. Their cross-coupling for the synthesis of useful isolable ketenimines remains an unsolved challenge in synthetic chemistry. Herein, we report a general method for the preparation of ketenimines via a palladium-catalyzed cross-coupling of easily accessible diazo compounds with isocyanides. The reaction benefits from the use of readily available starting materials, a wide substrate scope, high functional group tolerance, and a high yield in products, and the resultant ketenimines are amenable to further functionalization. Experimental findings and DFT calculations unambiguously corroborate the initial formation of a Pd(II)? isocyanide complex as the active catalytic species, which enables the cross-coupling reaction via a migratory insertion of Pd(II)? carbene into isocyanide, with evidence suggesting that the oxidation state of Pd(II) remains unchanged during the reaction.
