Organic Chemistry

Iron Catalyzed C-C Single Bond Cleavage of Alcohols

Authors

Abstract

An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage is developed under the irradiation of visible light, to produce ketones or aldehydes as the products. Linear alcohols and cycloalkanols with different ring sizes are suitable substrates, containing tertiary, secondary, and primary alcohols bearing a wide range of substitutes. Complex natural alcohols can also perform the transformation selectively. The mechanism investigation reveals an unpresented reaction procedure that involves chlorine radical as a key intermediate, which is generated from [FeCl4]- through ligand to metal charge transfer (LMCT). The study illustrates new possibilities for iron photocatalysis, especially for various deconstruction/functionalization reactions.

Version notes

Two reactions in table 3 in the absence of 2,4,6-collidine have been added, together with the relevant discussion.

Content

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Supplementary material

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Supporting Information of Iron catalyzed C-C single bond cleavage of alcohols
General Information, experimental details, 1H and 13C NMR Spectra of Products, and mechanistic study details.