Iron-catalyzed intermolecular [2π + 2π] cycloaddition

Sarah K. Russell; Emil Lobkovsky; Paul J. Chirik

doi:10.1021/ja202992p

Iron-catalyzed intermolecular [2π + 2π] cycloaddition

Sarah K. Russell
, Emil Lobkovsky
, Paul J. Chirik

Chemistry

Research output: Contribution to journal › Article › peer-review

143 Scopus citations

Abstract

The bis(imino)pyridine iron dinitrogen compounds, (^iPrPDI) Fe(N₂)₂ and [(^MePDI)Fe(N₂)] ₂(μ₂-N₂) (^RPDI = 2,6-(2,6-R ₂-C₆H₃N=CMe)₂C₅H ₃N; 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.

Original language	English (US)
Pages (from-to)	8858-8861
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	23
DOIs	https://doi.org/10.1021/ja202992p
State	Published - Jun 15 2011

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Iron-catalyzed intermolecular [2π + 2π] cycloaddition",

abstract = "The bis(imino)pyridine iron dinitrogen compounds, (iPrPDI) Fe(N2)2 and [(MePDI)Fe(N2)] 2(μ2-N2) (RPDI = 2,6-(2,6-R 2-C6H3N=CMe)2C5H 3N; 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.",

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doi = "10.1021/ja202992p",

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AU - Russell, Sarah K.

AU - Lobkovsky, Emil

AU - Chirik, Paul J.

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Y1 - 2011/6/15

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AB - The bis(imino)pyridine iron dinitrogen compounds, (iPrPDI) Fe(N2)2 and [(MePDI)Fe(N2)] 2(μ2-N2) (RPDI = 2,6-(2,6-R 2-C6H3N=CMe)2C5H 3N; 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.

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ER -

Iron-catalyzed intermolecular [2π + 2π] cycloaddition

Abstract

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