Ni/NHC-catalyzed C5-H alkylation and alkenylation of challenging furan(thiophene)-2-carboxaldehydes enabled by recyclable imine protecting group.

ABSTRACT: Transition-metal-catalyzed C-H alkylation of heteroaromatics with alkenes represents an atom-economical and cost-effective strategy for accessing industrially and pharmaceutically relevant compounds. However, the selective C5-H alkylation of biomass-derived furfural and its isosteric analog, thiophene-2-carboxaldehyde, highly challenging yet industrially vital substrates, has remained elusive. Herein, we disclose a Ni/NHC-catalyzed strategy for the C5-H alkylation of furan- and thiophene-2-carboxaldehydes with styrenes and norbornene, enabled by a readily installable and recyclable N-PMP (p-methoxyphenyl) imine protecting group. This method also achieves selective C5-H alkenylation with internal alkynes. Mechanistic studies suggest that C-H alkylation proceeds via a ligand-to-ligand hydrog

SUBMITTER: Khazipova OV 

PROVIDER: S-EPMC12373790 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature