Aryl Sulfoxides: A Traceless Directing Group for Catalytic C-H Activation of Arenes

Chempluschem. 2024 Mar 26:e202300728. doi: 10.1002/cplu.202300728. Online ahead of print.

Abstract

The transition metal-catalyzed C-H activation of arenes directed by sulfoxides represents a compelling strategy in organic synthesis, owing to its exceptional regioselectivity and high efficiency. This innovative approach stands out for its traceless character, enabling the direct functionalization of arenes, before the easy removal or conversion of the key sulfinyl moiety. Beyond their utility as a directing group, sulfoxides have proved particularly valuable to mediate as chiral auxiliaries, presenting exciting prospects for the synthesis of stereo-enriched compounds upon C-H functionalization. The versatility demonstrated by the method paves the way to different structures with potential applications ranging from medicinal chemistry to organic electronics.

Keywords: C−H activation; directing groups; homogeneous catalysis; sulfoxides; sulfur.