DBU-Mediated Oxidation of β-Dicarbonyls: Formation of Hydroxylated and Rearranged Products under Air Atmosphere

Synthesis DOI: 10.1055/a-2232-8776 The oxidation of different β-dicarbonyls in acetonitrile has been explored under an air atmosphere in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The presence of DBU resulted in the formation of hydroxylated products or rearrangement products derived from hydroxylated products. Specifically, the transformation of 2-oxocyclopentanecarboxylates to 2-hydroxyhexanedioates was achieved with good yields when additional 1,2-bis(diphenylphosphino)ethane and ROH were present. DBU proved to be indispensable for this transformation and showed specificity beyond its usual role as a base. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - January 24, 2024 Category: Chemistry Authors: Peng, Shuai Wang, Tianqi Zhao, Xixuan Yao, Boan Zhao, Kaishuo Liu, Yongguo Sun, Baoguo Tian, Hongyu Liang, Sen Tags: paper Source Type: research