Synthesis and Hydrosilylation of Furan and Thiophene N-Methylenefluoroanilines in the Presence of Pd(I) Complex

A series of new N-hetarylaldimines were synthesized by the reactions of furan and thiophene aldehydes with 2-, 3-, and 4-fluoroanilines in the presence of molecular sieves. The reaction of some of the synthesized azomethines with triethoxysilane in the presence of the [Pd(allyl)Cl]₂ complex was studied. It was found that the structure of the initial aldimines has an effect on the direction of hydrosilylation. All the studied substrates are transformed into the corresponding amines. The products of N- and C-silylation were also detected in the reaction mixtures. In certain cases reduction of the furan and thiophene rings occurs. Dedicated to Prof. N. S. Zefirov as a sign of respect in connection with his birthday __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1312–1319, September, 2005.