Convenient and fast desymmetrization of salen ligands may be achieved by reacting symmetrical Zn(salen) complexes with NBu4OH in CH3CN solution; the key features include very mild reaction conditions (r.t., no additives needed), short reaction times (5-10 min) and easy isolation (crystallization). The prominent step in this new protocol is the controlled hydrolysis of one of the imine bonds by hydroxide, and the resulting monoimine salts comprising both a phenolate anion and NBu4 counterion, are versatile reagents for the construction of multinuclear (chiral) metallosalen complexes that are useful in homogeneous catalysis and supramolecular applications. One such application will be highlighted where we used these reagents for the assembly of a bis-Zn(salphen) complex where the two Zn complexes are fused by a biphenyl spacer. This complex has been successfully applied in supramolecular chirogenesis using chiral carbozylic acids.

Zinc(II) mediated desymmetrization of (multi)salen ligands: Access to versatile reagents

242nd National Meeting (2011)

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