title: Palladium(II)-catalyzed intramolecular carboxypalladation-olefin insertion cascade: direct access to indeno[1,2-b]furan-2-ones.
abstract: A catalytic, atom-economical, domino 5-endo-dig cyclization-intramolecular olefin insertion sequence was developed under mild conditions. Aryl alkynoic acids bearing a tethered enone partner afforded the indeno[1,2-b]furan-2-ones, the core skeleton present in a number of biologically significant molecules including the natural product solanacol, under ligand-free, palladium-catalyzed reaction conditions in high yields. The competitive β-hydride elimination in the final step leading to the conjugated analogs was avoided by the addition of lithium bromide. A plausible mechanism for this domino sequence is proposed involving intramolecular carboxypalladation and olefin insertion steps.
authors: Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University, Thanjavur 613401, Tamil Nadu, India. vsridharan@scbt.sastra.edu vesridharan@gmail.com.
authors: Perumal
authors: P
authors: Vinoth
authors: Thavaraj
authors: T
authors: Vivekanand
authors: Padmakar A
authors: PA
authors: Suryavanshi
authors: J Carlos
authors: JC
authors: Menéndez
authors: Hiroaki
authors: H
authors: Sasai
authors: Vellaisamy
authors: V
authors: Sridharan
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000475:Alkenes; D005663:Furans; D010165:Palladium