Electrochemically reduced titanocene dichloride as a catalyst of reductive dehalogenation of organic halides

Abstract We have studied a reaction between the reduced form of titanocene dichloride (Cp 2 TiCl 2 ) and a group of organic halides: benzyl derivatives (4-X C 6 H 4 CH 2 Cl, X = H, NO 2 , CH 3 ; 4-X C 6 H 4 CH 2 Br, X = H, NO 2 , PhC(O); 4-X C 6 H 4 CH 2 SCN, X = H, NO 2 ) as well as three aryl halides (4-NO 2 C 6 H 4 Hal, Hal = Cl, Br; 4-CH 3 O-C 6 H 4 Cl). It has been shown that the electrochemical reduction of Cp 2 TiCl 2 in the presence of these benzyl halides leads to a catalytic cycle resulting in the reductive dehalogenation of these organic substrates to yield mostly corresponding toluene derivatives as the main product. No dehalogenation has been observed for aryl derivatives. Base…