Selective cleaving the NP bond of difluoromethylene phosphabetaines for effective synthesis of β-ketoamides. Issue 29 (18th July 2019)

• Record Type: Journal Article
• Authors: Liu, Yingle; Yang, Tao; Dong, Yuting; Cai, Junjie; Luo, Gen; Tong, Xia; Jiang, Yan; Yang, Yi; Xu, Xiu-Hua
• Is Part Of: Tetrahedron letters. Volume 60:Issue 29(2019)
• Page Start: 1934
• Page End: 1937
• Publication Date: 2019-07-18
• Subjects: Difluoromethylene phosphabetaines -- β-Ketoamides -- β-Ketoester -- Aminating reagent; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.06.036
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: [Tris(dimethylamino)phosphonio]difluoroacetate ADFA is a novel aminating reagent. Selective cleaving NP bond of ADFA. An transition-metal and base-free protocol for the synthesis of β-ketoamides. Simple operation and wide substrate scope. Abstract: An unprecedent transition-metal-free protocol for the synthesis of β-ketoamides from β-ketoesters is described. This method involves selective cleaving NP bond of an unusual aminating reagent, [tris(dimethylamino)phosphonio]difluoroacetate (ADFA), which is well known as the difluoromethylene ylide precursor. The process is notable for its operational simplicity and good functional group tolerance.