Cobalt-Catalyzed N–O and C–C Bond Cleavage in 1,2-Oxazetidines: Solvent-Controlled C–H Aminomethylation and Hydroxymethylation of Heteroarenes

• DOI: 10.1021/acs.orglett.9b00141
• Publication Date: 2019-02-26T19:39:37Z
• Authors: Song Li; Pengfei Shi; Rui-Hua Liu; Xu-Hong Hu; Teck-Peng Loh
• Keywords: Cleavage (geology); Bond cleavage

An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp*Co(III) catalyst enables a distinctive merger C–H activation concomitant N–O and C–C cleavages 1,2-oxazetidine, leading to site-selective aminomethylation hydroxymethylation heteroaromatic compounds containing broad range functional groups. Preliminary control experiments unravel some essential mechanistic features this one-pot transformation.