A facile transesterification route to ferrocenyl esters

In the presence of tetrabutylammonium hydroxide as catalyst and at room temperature, ethyl ferrocenecarboxylate, ethyl ferrocenylacetate, ethyl 3-ferrocenylpropanoate, 1,1′-ferrocenyl-bis(ethyl propanoate), ethyl 3-ferrocenylpropenoate and 1,1′-ferrocenyl-bis(ethyl propenoate) undergoes facile transesterification reaction with aliphatic, benzyl and allyl alcohols to furnish the corresponding ferrocenyl esters in good to excellent yields. Ring closing metathesis of the ester Fc-1,1′-(CHCH–CO2CH2CHCH2)2 yields the corresponding closed loop ferrocenyl ester.

Graphical abstractIn the presence of catalytic tetrabutylammonium hydroxide (20 mol%) and at room temperature, ethyl ferrocenecarboxylate, ethyl ferrocenylacetate, ethyl 3-ferrocenylpropanoate, 1,1′-ferrocenyl-bis(ethyl propanoate), ethyl 3-ferrocenylpropenoate and 1,1′-ferrocenyl-bis(ethyl propenoate) undergoes facile transesterification reaction with aliphatic, benzyl and allyl alcohols to furnish the corresponding ferrocenyl esters in good to excellent yields. Ring closing metathesis of the ester Fc-1,1′-(CHCH–CO2CH2CHCH2)2 yields the corresponding closed loop ferrocenyl ester.Figure optionsDownload full-size imageDownload as PowerPoint slide