Aerobic Direct Dioxygenation of Terminal/Internal Alkynes to α‐Hydroxyketones by an Fe Porphyrin Catalyst. Issue 22 (28th September 2021)

• Record Type: Journal Article
• Authors: Kimura, Kento; Kurahashi, Takuya; Matsubara, Seijiro
• Is Part Of: Chemistry, an Asian journal. Volume 16:Issue 22(2021)
• Page Start: 3615
• Page End: 3618
• Publication Date: 2021-09-28
• Subjects: oxidation -- alkyne -- α-hydroxyketone -- ferric porphyrin complex -- compound 0; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.202101019
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: We herein report a new synthetic method for the preparation of α‐hydroxyketones by the dioxygenation of alkynes. The reaction proceeds at room temperature under the action of Fe porphyrin and pinacolborane under air as a green oxidant to produce α‐hydroxyketones. The mild reaction conditions allow chemoselective oxidation with functional group tolerance. Terminal alkynes in addition to internal alkynes are applicable, affording unsymmetrical α‐hydroxyketones that are difficult to obtain by any reported dioxygenation of unsaturated C−C bonds. Abstract : The synthesis of α‐hydroxyketones through the dioxygenation of alkynes is reported. The reaction is mediated by an Fe porphyrin complex and pinacolborane at room temperature under air as a green oxidant, furnishing α‐hydroxyketones in up to 93% yields. The mild reaction conditions allow chemoselective oxidation with good functional group tolerance.