Pd-Catalyzed Reactions of Donor−Acceptor-Substituted Cyclopropanes and Their Ring-Opened Derivatives: Attempted Heck Cyclization and Novel One-Pot Enolate Arylations

Abstract

Donor−acceptor substituted cyclopropane derivatives 4a−g were synthesized in good yields from ketones, via the corresponding silyl enol ethers 2a−g, by cyclopropanation with methyl diazoacetate followed by alkylation using o-iodobenzyl iodide. The γ-oxo esters 5a−g were prepared in high yield, employing NEt 3 · 3 HF. A novel Pd-catalyzed one-pot transformation of 4a−f into 1,2-disubstituted indanes 6a−f was accomplished using either CsF (Method A or B) or Bu 4 NF (Method C) as the fluoride source to achieve the in [a]

Iron‐Catalyzed Homo‐Coupling of Simple and Functionalized Arylmagnesium Reagents.

“…1 H, 13 C and 19 F NMR spectra were recorded on JEOL EX-270 and JEOL ECX-400 spectrometers. Chemical shifts δ are given in ppm from TMS as an internal reference.…”