Zirconium-Catalyzed Remote Defunctionalization of Alkenes

This work introduces a catalytic zirconium chain-walk reaction that in combination with a beta-heteroatom elimination step enables the cleavage of remote nonactivated carbon-heteroatom bonds. The result is a controlled defunctionalization reaction, which takes place with excellent site selectivity and can be applied to symmetrical and unsymmetrical alkene chains with ether, amine, and thioether groups. The approach can be used for remote functional group substitution as well, and a preliminary investigation indicates a dissociative chain-walk mechanism.