New synthesis of acylferrocene by hydroiminoacylation of the terminal olefin with ferrocenecarboxaldimine and application to polymer-supported acylferrocene

Acylferrocenes were synthesized by hydroiminoacylation of the ω-olefins 1-pentene (3a), vinylferrocene (3b) and but-3-enylferrocene (3c), with the ferrocenecarboxaldimine 2, prepared from ferrocenecarboxaldehyde (1) and 2-amino-3-picoline, under the action of Wilkinson's catalyst, followed by hydrolysis of the corresponding ketimines (5a, 5b and 5c). This hydroiminoacylation was used to incorporate the ferrocenyl group into phenyl-terminated poly-butadiene (PTPB, consisting of 27% vinyl and 73% internal olefin group). 74% hydroacylation of the vinyl group in 7 was accomplished in the first catalytic reaction and in 10 the second hydroacylation completed the conversion of the vinyl group into acylferrocene.