1-vinylimidazole - a versatile building block for the synthesis of cationic phosphines useful in ionic liquid biphasic catalysis

Base catalyzed addition of 1-vinylimidazole to primary and secondary phosph ines affords tertiary phosphines with terminal 1-imidazolyl substituents C3 H3N2 in high yields. The X-ray structure of the oxide Ph2P(O)-(CH2)(2)-1-C3 H3N2 has been determined (space group Pi). By selective N-protonation and p rotected group N-quaternization novel cationic phosphines, e.g. 2a, 2b, 9 a nd 10, with peripheral 1-imidazolium groups are obtained. These are interes ting ligands for catalytic reactions in biphasic systems containing ionic l iquids as polar phase and may be employed in, hydroformylation of long-chai n olefins like 1-octene. (C) 2001 Elsevier Science B.V. All rights reserved .