Iron-Catalyzed Intermolecular [2π + 2π] Cycloaddition

The bis(imino)pyridine iron dinitrogen compounds, (iPrPDI)Fe(N2)2 and [(MePDI)Fe(N2)]2(μ2-N2) (RPDI = 2,6-(2,6-R2-C6H3NCMe)2C5H3N; R = iPr, Me), promote the catalytic intermolecular [2π + 2π] cycloaddition of ethylene and butadiene to form vinylcyclobutane. Stoichiometric experiments resulted in is...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2011-06, Vol.133 (23), p.8858-8861
Main Authors: Russell, Sarah K, Lobkovsky, Emil, Chirik, Paul J
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The bis(imino)pyridine iron dinitrogen compounds, (iPrPDI)Fe(N2)2 and [(MePDI)Fe(N2)]2(μ2-N2) (RPDI = 2,6-(2,6-R2-C6H3NCMe)2C5H3N; R = iPr, Me), promote the catalytic intermolecular [2π + 2π] cycloaddition of ethylene and butadiene to form vinylcyclobutane. Stoichiometric experiments resulted in isolation of a catalytically competent iron metallocycle intermediate, which was shown to undergo diene-induced C–C reductive elimination. Deuterium labeling experiments establish competitive cyclometalation of the bis(imino)pyridine aryl substituents during catalytic turnover.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja202992p