Potassium methoxide/disilane-mediated formylation of aryl iodides with DMF at room temperature

Abstract

A formylation of aryl iodides at room temperature using a weaker base KOMe instead of BuLi was developed. The TMS-TMS disilane was discovered to play crucial roles in this formylation. It was found that the MeO⁻ group of KOMe coordinated with two silyl groups of disilane to generate a hypercoordinate silane species. This hypercoordinate silane species reacted with aryl iodide to give an aryl carbanion, which underwent formylation with DMF to give an aryl aldehyde.