Multipurpose sulfoximine-mediated radical γ-heteroarylation of unactivated C(sp3)-H bonds.

A conceptually novel, trifunctional sulfoximine-mediated γ-functionalization of unactivated C(sp³)-H bonds has been achieved. The reaction is initiated by the photo-induced homolytic cleavage of an N-S bond in the absence of photosensitizer, and proceeds sequentially through a cascade of 1,5-hydrogen atom transfer, 1,4-functional group migration, desulfoximination and a Minisci reaction. A major feature of this approach is the use of sulfoximine as a traceless directing group. Other positive properties include mild conditions, simple operation, exclusive site-selectivity, high product diversity and the avoidance of additional photosensitizers. The protocol provides a new reaction mode for HAT-induced C(sp³)-H functionalization, and allows a much broader chemical space for sulfoximine studies. [ABSTRACT FROM AUTHOR]