Chiral bisimidazolium salts derived from amino acids and their palladium(II)- and platinum(II)-biscarbene complexes

We report new chiral bisimidazolium salts synthesized from naturally occurring l-amino acids. They served as precursors for bidentate N-heterocyclic carbene metal complexes. The chiral imidazoles could be synthesized in good yields via a one-pot ring closing reaction, followed by esterification. The methylene bridged bisimidazolium iodide salts are accessible in moderate yields. Corresponding palladium(II)- and platinum(II)-NHC complexes could be synthesized and fully characterized, but do not show optical activity. We also report a solid state structure of one of the synthesized palladium(II) biscarbene compounds derived from alanine.

Graphical abstractChiral imidazoles and bidentate imidazolium iodide salts have been synthesized from naturally occurring l-amino acids. The synthesis of palladium(II)- and platinum(II) N-heterocyclic biscarbene complexes is described.Figure optionsDownload full-size imageDownload as PowerPoint slide