Regioselective differentiation of vicinal methylene C-H bonds enabled by silver-catalysed nitrene transfer.

ABSTRACT: Silver-catalyzed nitrene insertion enables the formation of benzosultams in good yield and with regioselectivity complementary to other transition metal nitrene-transfer catalysts. Preferential formation of six-membered benzosultam rings predominates for alkyl-substituted benzenesulphonamide precursors. Ligand-controlled tunability is also achieved for benzenesulphonamides with γ-branched alkyl substituents. Mechanistic probes suggest that the reaction pathway differs depending on whether a α (benzylic) or β (homobenzylic) C-H bond undergoes amidation, as well as the catalyst identity.

SUBMITTER: Scamp RJ 

PROVIDER: S-EPMC6613557 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature