Xiaoyin Yang

Selective functionalization of imidazoles via an iodine–copper exchange reaction

The reaction of protected 4,5-diiodoimidazoles with (PhMe2CCH2)2CuLi regioselectively provides 5-cuprated imidazoles, which readily react with various electrophiles furnishing functionalized imidazoles in good yields; remarkably, these resulting mono-iodoimidazoles undergo again an iodine-copper exchange reaction in the presence of sensitive functional groups, like an aldehyde or a ketone.

Direct preparation of copper organometallics bearing an aldehyde function via an iodine-copper exchange.

The iodine-copper exchange reaction allows the direct preparation of various aryl, heteroaryl and alkenyl cuprates bearing a formyl group, thus allowing a direct synthesis of polyfunctional aldehydes without the need of protecting groups or an additional oxidation step.

Stereoselective Preparation of Highly Functionalized (Z)-3-Copper Enoates by an Iodine-Copper Exchange Reaction

3-Iodoenoates are readily converted into the corresponding alkenylcopper species with complete retention of configuration of the double bond via an iodine-copper exchange reaction. Quenching reactions with various electrophiles provide highly functionalized enoates in good yields.