Iron-catalyzed amidation of 1,3-dicarbonyl compounds.

• Main Author: Ong, Wei Ting.
• Other Authors: Philip Wai Hong Chan
• Format: Final Year Project
• Language: English
• Published: 2010
• Subjects: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
• Online Access: http://hdl.handle.net/10356/39882
• Institution: Nanyang Technological University

An efficient Fe-catalyzed amidation of 1,3-dicarbonyl compounds to α-amidated products through C(sp3)-H functionalization is achieved via 2 methods; indirect method of using PhI=NTs (Ts = toluene-4-sulfonyl) as nitrogen source and direct method of using PhI(OAc)2 as oxidant and TsNH2 as nitrogen source. The reaction was applied successfully to a variety of aromatic and aliphatic 1,3-dicarbonyl compounds with electron-donating, electron-withdrawing and sterically encumbered groups present in the substrates. The amidated products were obtained in excellent yields up to 99% under mild conditions at room temperature.