jo052085y_si_005.pdf (1.41 MB)
Acetyltrimethylsilane: A Novel Reagent for the Transformation of 2H-Pyran-2-ones to Unsymmetrical Biaryls†
journal contributionposted on 2006-01-20, 00:00 authored by Atul Goel, Deepti Verma, Manish Dixit, Resmi Raghunandan, P. R. Maulik
An expeditious synthesis of unsymmetrical biaryls functionalized with electron-withdrawing or -donating substituents is described and illustrated by carbanion-induced ring transformation of 2H-pyran-2-one using acetyltrimethylsilane (ATMS) as a novel reagent in good yield. The novelty of the reaction lies in the creation of an aromatic ring from 2H-pyran-2-ones via two-carbon insertion from ATMS used as a source of carbanion.