Jump to main content
Jump to site search


Ni-Catalysed Intramolecular [4+4]-cycloadditions of bis-dienes towards eight-membered fused bicyclic systems: a combined experimental and computational study

Author affiliations

Abstract

Detailed investigations on the use of nickel(0)-based catalysts for intramolecular [4+4]-cycloadditions are presented. Nickel(0) complexes derived from electron-rich triarylphosphines proved to be efficient catalysts for intramolecular [4+4]-cycloadditions of an array of structurally diverse bis-dienes (10 examples, up to 78% isolated yield). The reported synthetic methodology leads to cis-eight-membered fused [6.3.0] bicyclic compounds as well as trans- or cis-eight-membered fused [6.4.0] bicyclic systems. Computational studies on the stereo-determining step of the reaction in combination with experimental results demonstrated that the stereochemical outcome is dictated by the length of the chain linking the two diene units and the geometry of the C[double bond, length as m-dash]C double bonds of the substrates.

Graphical abstract: Ni-Catalysed Intramolecular [4+4]-cycloadditions of bis-dienes towards eight-membered fused bicyclic systems: a combined experimental and computational study

Back to tab navigation

Supplementary files

Publication details

The article was received on 05 Apr 2018, accepted on 05 Sep 2018 and first published on 10 Sep 2018


Article type: Paper
DOI: 10.1039/C8CY00684A
Citation: Catal. Sci. Technol., 2018, Advance Article
  •   Request permissions

    Ni-Catalysed Intramolecular [4+4]-cycloadditions of bis-dienes towards eight-membered fused bicyclic systems: a combined experimental and computational study

    N. Llorente, H. Fernández-Pérez, A. Bauzá, A. Frontera and A. Vidal-Ferran, Catal. Sci. Technol., 2018, Advance Article , DOI: 10.1039/C8CY00684A

Search articles by author

Spotlight

Advertisements