4.8 Article

Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols

Journal

ORGANIC LETTERS
Volume 23, Issue 21, Pages 8413-8418

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03137

Keywords

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Funding

  1. Department of Science and Technology of Guangdong Province [2019QN01L151]
  2. National Natural Science Foundation of China [21821003]
  3. Sun Yat-Sen University

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An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage has been developed via photocatalysis, yielding ketones or aldehydes as products. This process is applicable to tertiary, secondary, and primary alcohols with a wide range of substituents, including complex natural alcohols. Investigating the mechanism uncovered a process involving chlorine radical-enhanced O-H homolysis, assisted by 2,4,6-collidine.
An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage is developed through photocatalysis, to produce ketones or aldehydes as the products. Tertiary, secondary, and primary alcohols bearing a wide range of substituents are suitable substrates. Complex natural alcohols can also perform the transformation selectively. A investigation of the mechanism reveals a procedure that involves chlorine radical improved O-H homolysis, with the assistance of 2,4,6-collidine.

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