Controlled reductive C-C coupling of isocyanides promoted by an aluminyl anion.

ABSTRACT: We report the reaction of the potassium aluminyl, K[Al(NON)] ([NON]^2- = [O(SiMe₂NDipp)₂]^2-, Dipp = 2,6-iPr₂C₆H₃) with a series of isocyanide substrates (R-NC). In the case of tBu-NC, degradation of the isocyanide was observed generating an isomeric mixture of the corresponding aluminium cyanido-κC and -κN compounds, K[Al(NON)(H)(CN)]/K[Al(NON)(H)(NC)]. The reaction with 2,6-dimethylphenyl isocyanide (Dmp-NC), gave a C₃-homologation product, which in addition to C-C bond formation showed dearomatisation of one of the aromatic substituents. In contrast, using adamantyl isocyanide Ad-NC allowed both the C₂- and C₃-homologation products to be isolated, allowing a d

SUBMITTER: Evans MJ 

PROVIDER: S-EPMC10266456 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature