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Iron-Catalyzed [2π + 2π] Cycloaddition of α,ω-Dienes: The Importance of Redox-Active Supporting Ligands

Supporting Info

Marco W. Bouwkamp, Amanda C. Bowman, Emil Lobkovsky, and Paul J. Chirik*

Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14850

J. Am. Chem. Soc., 2006, 128 (41), pp 13340–13341

DOI: 10.1021/ja064711u

Publication Date (Web): September 22, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pc92@cornell.edu

Abstract

The bis(imino)pyridine iron bis(dinitrogen) complex, (ⁱPrPDI)Fe(N₂)₂ (ⁱPrPDI = 2,6-(2,6-ⁱPr₂C₆H₃NCR)₂C₅H₃N), serves as an efficient precursor for the catalytic [2π + 2π] cycloaddition of α,ω-dienes to yield the corresponding bicycles. For amine substrates, the rate of catalytic turnover increases with the size of the nitrogen substituents, demonstrating competing heterocycle coordination and product inhibition. In one case, a bis(imino)pyridine iron azobicycloheptane product was characterized by X-ray diffraction. Preliminary mechanistic studies highlight the importance of the redox activity of the bis(imino)pyridine ligand to maintain the ferrous oxidation state throughout the catalytic cycle.

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Published In Issue October 18, 2006
Received July 3, 2006

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Communication

Iron-Catalyzed [2π + 2π] Cycloaddition of α,ω-Dienes: The Importance of Redox-Active Supporting Ligands

Abstract

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History

Recommend & Share

Related Content

Preparation and Molecular and Electronic Structures of Iron(0) Dinitrogen and Silane Complexes and Their Application to Catalytic Hydrogenation and Hydrosilation

Iron-Catalyzed 1,4-Addition of α-Olefins to Dienes

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