Aerobic Photoredox Catalyzed Oxamate Ester Synthesis from Bromodifluoroacetate Esters

• Published in: European journal of organic chemistry 2024-06, Vol.27 (23), p.n/a
• Main Authors: Tagami, Takuma, Kawamura, Shintaro, Sodeoka, Mikiko
• Format: Article
• Language: English
• Subjects: Amines; Catalysis; Chemical synthesis; Esters; Oxygenation; Photocatalysis; Photoredox catalysis; Precursors; Radical reactions; Synthetic methods
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202400265

Here we report an aerobic photoredox catalysis approach to oxamate ester synthesis using bromodifluoroacetate esters and amines under open‐air conditions. Oxamate ester is an important skeleton found in bioactive molecules and used as a synthetic building block. However, previous synthetic methods require the use of moisture‐ and air‐sensitive precursors and/or harsh conditions, limiting accessible oxamate esters. The present method uses bench‐stable bromodifluoroacetate esters and amines under mild photoredox catalytic conditions to furnish a wide variety of oxamate esters. Combining photoredox catalysis with aerobic oxygenation enables the use of bromodifluoroacetate ester as a precursor for the synthesis of oxamate esters via fluoroglyoxylate esters. We present a novel synthetic method for oxamate esters using bromodifluoroacetate esters and amines under aerobic photoredox catalysis. In contrast to previous methods that require the use of moisture‐sensitive precursors and/or harsh conditions, this method utilizes bench‐stable bromodifluoroacetate esters as an oxamate ester precursor under mild conditions, providing a variety of oxamate esters.