Application of pentacoordinated spirophosphorane as a new organocatalyst for the Michael addition reaction. (3rd October 2021)

• Record Type: Journal Article
• Authors: Wang, Peipei; Li, Wanjiao; Han, Kehui; Guo, Yanchun; Zhao, Yufen; Cao, Shuxia
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 196:Number 10(2021)
• Page Start: 936
• Page End: 947
• Publication Date: 2021-10-03
• Subjects: Pentacoordinated spirophosphorane -- organocatalyst -- Michael addition reaction -- catalytic mechanism -- hydrogen bonds; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2021.1946062
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: Pentacoordinated spirophosphorane as a simple, effective and novel organocatalyst for the Michael addition reaction has been investigated. The bisaminoacyl spirophosphorane that possessed a thiourea-like moiety and an amine group was applied to the Michael addition reaction of 1, 3-dicarbonyl compound with β-nitrostyrene, affording the desired adduct in good yield. Furthermore, the mechanism of the Michael addition reaction catalyzed by spirophosphorane was proposed with the help of the analysis of single crystal structure, NMR experiments. It was identified that 1, 3-dicarbonyl compound and β-nitrostyrene formed hydrogen bonds with amine group and N-H groups of spirophosphorane catalyst, respectively. Then the two reactants approached each other, and the methylene of 1, 3-dicarbonyl compound attacked the olefin carbon of β-nitrostyrene to form nucleophilic addition product. This report is the first example of spirophosphorane as a novel organocatalyst to successfully catalyze the Michael addition reaction. Graphical Abstract: Abstract : UF0001