Decarboxylative Oxygenation via Photoredox Catalysis. Issue 3 (13th December 2019)

• Record Type: Journal Article
• Authors: Faraggi, Tomer M.; Li, Wei; MacMillan, David W. C.
• Is Part Of: Israel journal of chemistry. Volume 60:Issue 3/4(2020)
• Page Start: 410
• Page End: 415
• Publication Date: 2019-12-13
• Subjects: photoredox catalysis -- oxygenation -- carbonyl synthesis -- decarboxylation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/ijch.201900130
• Languages: English
• ISSNs: 0021-2148

Abstract

Abstract: The direct conversion of aliphatic carboxylic acids to their dehomologated carbonyl analogues has been accomplished through photocatalytic decarboxylative oxygenation. This transformation is applicable to an array of carboxylic acid motifs, producing ketones, aldehydes, and amides in excellent yields. Preliminary results demonstrate that this methodology is further amenable to aldehyde substrates via in situ oxidation to the corresponding acid and subsequent decarboxylative oxygenation. We have exploited this strategy for the sequential oxidative dehomologation of linear aliphatic chains. Abstract : Oxidative decarboxylation of aliphatic carboxylic acids, followed by oxygen trapping of the resultant radical, is harnessed as a strategy for the synthesis of carbonyl compounds. This procedure enables the synthesis of a broad array of carbonyl products, and application to the oxidative degradation of aliphatic chains via sequential oxidation‐decarboxylation has been demonstrated.