2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(0)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon−nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.

Carbopalladation of Nitriles: Synthesis of 2,3-Diarylindenones and Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulation of Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles

Chiral Diene as the Ligand for the Synthesis of Axially Chiral Compounds via Palladium-Catalyzed Suzuki−Miyaura Coupling Reaction

Bonding and reactivity of cyclopentene on Pt(111)

Publisher Summary This chapter reviews the structural implications of the vibrational spectroscopic results from the adsorption of ethene and the higher alkenes on different metal surfaces. Alkenes are chosen because the spectra of their adsorbed species have been investigated in most detail. The emphasis has been on an exploration of the structures of the temperature-dependent chemisorbed species on different metal surfaces. The emphasis has been on an exploration of the structures of the temperature-dependent chemisorbed species on different metal surfaces. Particular attention has been directed to the spectra obtained on finely divided (oxide-supported) metal catalysts. The chapter also presents reviews of the fewer spectra from other families of adsorbed hydrocarbons, i.e., the alkynes, the alkanes (acyclic and cyclic), and aromatic hydrocarbons. Knowledge of the chemisorbed species present on a surface provides an essential database for the investigation of catalytic and other reaction mechanisms in which they are involved. The elucidation of reaction mechanisms in turn requires studies of chemical kinetics. An increasing number of such kinetic studies are now being made which involve vibrational spectroscopy and hydrocarbon adsorbates.

Vibrational Spectra of Hydrocarbons Adsorbed on Metals: Part I. Introductory Principles, Ethylene, and the Higher Acyclic Alkenes

Vibrational Spectra of Hydrocarbons Adsorbed on Metals: Part II. Adsorbed Acyclic Alkynes and Alkanes Cyclic Hydrocarbons Including Aromatics and Surface Hydrocarbon Groups Derived from the Decomposition of Alkyl Halides etc

D.W. Wertz

Papers

A vibrational study of the metal—olefin bond in norbornadiene complexes of Rh(I), Pd(II) and Pt(II)

A vibrational investigation of several platinum and palladium cyclopentene complexes