ORGANIC CHEMISTRY. Iron-catalyzed intermolecular [2+2] cycloadditions of unactivated alkenes

Science
Jordan M HoytPaul J Chirik

Abstract

Cycloadditions, such as the [4+2] Diels-Alder reaction to form six-membered rings, are among the most powerful and widely used methods in synthetic chemistry. The analogous [2+2] alkene cycloaddition to synthesize cyclobutanes is kinetically accessible by photochemical methods, but the substrate scope and functional group tolerance are limited. Here, we report iron-catalyzed intermolecular [2+2] cycloaddition of unactivated alkenes and cross cycloaddition of alkenes and dienes as regio- and stereoselective routes to cyclobutanes. Through rational ligand design, development of this base metal-catalyzed method expands the chemical space accessible from abundant hydrocarbon feedstocks.

References

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Citations

Feb 4, 2016·Inorganic Chemistry·Hiromasa TanahashiKazushi Mashima
Sep 1, 2015·Science·Myles W Smith, Phil S Baran
May 10, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Benjamin R M Lake, Michael P Shaver
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Jun 27, 2017·Journal of the American Chemical Society·Huiling JiangX Peter Zhang
Jul 7, 2017·Journal of the American Chemical Society·Mikhail V TsurkanCarsten Werner
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Nov 15, 2016·Acta Crystallographica. Section E, Crystallographic Communications·Ka-Cheong LauRichard F Jordan

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