Iridium-Catalyzed and pH-Dependent Reductions of Nitroalkenes to Ketones.

ABSTRACT: A highly chemoselective conversion of α,β-disubstituted nitroalkenes to ketones is developed. An acid-compatible iridium catalyst serves as the key to the conversion. At a 2500 S/C ratio, nitroalkenes were readily converted to ketones in up to 72% isolated yields. A new mechanistic mode involving the reduction of nitroalkene to nitrosoalkene and N-alkenyl hydroxylamine is proposed. This conversion is ready to amplify to a gram-scale synthesis. The pH value plays an indispensable role in controlling the chemoselectivity.

SUBMITTER: Wang T 

PROVIDER: S-EPMC9696932 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature