Oxidant-Free Conversion of Cyclic Amines to Lactams and H2 Using Water As the Oxygen Atom Source

JR Khusnutdinova, Y Ben-David…

Index: Khusnutdinova, Julia R.; Ben-David, Yehoshoa; Milstein, David Journal of the American Chemical Society, 2014 , vol. 136, # 8 p. 2998 - 3001

Full Text: HTML

Citation Number: 36

Abstract

Direct conversion of cyclic amines to lactams utilizing water as the only reagent is catalyzed by pincer complex 2. In contrast to previously known methods of amine-to-amide conversion, this reaction occurs in the absence of oxidants and is accompanied by liberation of H2, with water serving as a source of oxygen atom. Formation of a cyclic hemiaminal intermediate plays a key role in enabling such reactivity. This represents an unprecedented, ...

The Catalytic Hydrogenation of Esters to Alcohols. II

[Folkers; Adkins Journal of the American Chemical Society, 1932 , vol. 54, p. 1146]

Synthesis and reactivity of methyl γ-azido butyrates and ethyl σ-azido valerates and of the corresponding acid chlorides as useful reagents for the aminoalkylation

[Khoukhi, N.; Vaultier, M.; Carrie, R. Tetrahedron, 1987 , vol. 43, # 8 p. 1811 - 1822]

An aza-enolate alkylation strategy for the synthesis of α-alkyl-δ-amino esters and α-alkyl valerolactams

[Taylor, Piers J. M.; Bull, Steven D.; Andrews, Philip C. Synlett, 2006 , # 9 p. 1347 - 1350]