Diversification of NH‐Aryl Sulfoximines through Iridium‐Catalyzed ortho‐ and meta‐Selective C−H Borylation

Abstract

Herein, the selective ortho‐ and meta‐C−H bond borylation of NH‐aryl sulfoximines is reported. Regioselectivity is achieved by the choice of commercially available ligands giving fast excess to valuable borylated aryl sulfoximine building blogs. The utility of the borylated products is demonstrated for the formation of C−O, C−C, C−N, C−D, and C−I bonds.

Synthesis of Benzo[e][1,4,3]oxathiazin-3-one 1-Oxides from NH-S-(2-Hydroxyaryl)sulfoximines

“…Alternatively, compounds 3 could be prepared by o-C−H bond borylation and subsequent oxidation starting from NH-S-(aryl)sulfoximines 4 (Scheme 1). 11 Next, the cyclization of compounds 3 to give 5 (=IV) was investigated. For the optimization of the reaction conditions, NH-S-(2-hydroxyphenyl)-S-methyl sulfoximine (3a) and 1,1′carbonyldiimidazole (CDI) were chosen as the representative substrate and carbonyl source, respectively.…”