Aerobic α-hydroxylation of β-keto esters and amides by co-catalysis of SmI3 and I2 under mild base-free conditions. Issue 25 (22nd June 2016)

• Record Type: Journal Article
• Authors: Yu, Shun-Ming; Cui, Kai; Lv, Fei; Yang, Zhen-Yu; Yao, Zhu-Jun
• Is Part Of: Tetrahedron letters. Volume 57:Issue 25(2016)
• Page Start: 2818
• Page End: 2821
• Publication Date: 2016-06-22
• Subjects: Aerobic oxidation -- 1, 3-Dicarbonyl compound -- Samarium(III) iodide -- Free radical -- Catalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.052
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Clean base-free α-hydroxylation of β-keto esters and amides with air. The first report of new binary catalytic system of SmI3 and I2 . Wide scope of substrates, excellent yields, and mild conditions. Both oxygen atoms of dioxygen are utilized and incorporated into the product through a unique free-radical process. Abstract: A clean base-free α-hydroxylation of β-keto esters and amides has been developed, in which air was used as the oxygen source and SmI3 and I2 were applied as the catalysts, affording the corresponding α-hydroxylated 1, 3-dicarbonyl products in good to excellent yields under mild conditions. Mechanism discussion shows that both oxygen atoms of dioxygen are utilized and incorporated into the product through a unique free-radical process.