Nickel(0)-Catalyzed [2 + 2 + 2 + 2] Cycloadditions of Terminal Diynes for the Synthesis of Substituted Cyclooctatetraenes

2007/10/11 by Paul A. Wender, Justin P. Christy · 2 citations
Chemistry · #Catalytic Alkyne Reactions #Cyclopropane Reaction Mechanisms #Synthetic Organic Chemistry Methods

paper · doi:10.1021/ja0763044

openalex publication_date 2007/10/11 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

The Ni(0)-catalyzed [2 + 2 + 2 + 2] cycloadditions of 1,6- and 1,7-diynes are shown to provide an efficient and selective method for the preparation of 1,2,5,6-tetrasubstituted cyclooctatetraenes (COTs). Catalysts and conditions are described that favor in all cases COT formation over competing [2 + 2 + 2] cycloadditions. A hitherto unexplored crossed reaction is also described, providing access to non-symmetrical COTs.

Cited by

• Dichlorobis(triphenylphosphine)nickel(II)
• Organonickel chemistry [wikipedia]

Related

• Selective synthesis of cyclic alcohols from cycloalkanes using nickel( ii ) complexes of tetradentate amidate ligands
• Metal Complexes of Small Cycloalkynes and Arynes
• Formation of an Aza‐nickelacycle by Reaction of an Imine and an Alkyne with Nickel(0): Oxidative Cyclization, Insertion, and Reductive Elimination
• Recent developments in nickel-catalyzed intermolecular dicarbofunctionalization of alkenes
• Nickel-Catalyzed Dicarbofunctionalization of Alkenes