Negishi Cross-Coupling of Sulfonyl Chlorides

Significance

This is an interesting new example of a transition-metal-catalyzed C-C bond-forming reaction. The coupling proceeds smoothly between aryl sulfonyl chlorides and arylzinc compounds, and to some extent also with alkenyl and allylzinc species. The reaction is practical and uses a commercially available catalyst. It presents a significant interest from the methodological point of view, since it proceeds via an unusual palladium insertion into the S-Cl bond of a sulfonyl chloride, and might lead to a new general novel synthetically useful method of C-C bond formation.