Issue 20, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
05 Apr 2018
Accepted
05 Sep 2018
First published
10 Sep 2018

Catal. Sci. Technol., 2018,8, 5251-5258

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, 8, 5251 DOI: 10.1039/C8CY00684A

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