4.8 Article

Visible-Light Mediated Oxidative Fragmentation of Ethers and Acetals by Means of Fe(III) Catalysis

Journal

ORGANIC LETTERS
Volume 24, Issue 8, Pages 1662-1667

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00231

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Funding

  1. Swedish Research Council
  2. Swedish NMR Centre at the University of Gothenburg

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A new method using iron(III) acetylacetonate and visible light has been described to efficiently achieve oxidative ring opening of cyclic ethers and acetals. This approach enables the functionalization of relatively inert cyclic ethers into useful synthetic intermediates through photocatalytic radical chemistry. The study also highlights the potential of using underexplored iron complexes in visible-light photochemical reactions, demonstrating that simple Fe(III) complexes can initiate redox processes from (LMCT)-L-4 excited states.
A new method employing iron(III) acetylacetonate along with visible light is described to effect oxidative ring opening of cyclic ethers and acetals with unparalleled efficiency. The method allows for a photocatalytic radical chemistry approach to functionalize relatively inert cyclic ethers into useful synthetic intermediates. The methodology sheds further light on the use of underexplored iron complexes in visible-light photochemical contexts and illustrates that simple Fe(III) complexes can initiate redox processes from (LMCT)-L-4 excited states.

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