Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

• Youlong Du,
• Haibo Mei,
• Ata Makarem,
• Ramin Javahershenas,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2024, 20, 212–219, doi:10.3762/bjoc.20.21

• efficient way for the synthesis of β-trifluoromethyl β-diacylamino esters. Furthermore, this reaction represents the first example of a Mumm rearrangement of β-trifluoromethyl β-diazo esters. Keywords: β-carbonyl diazo; copper catalyst; fluoroalkyl diazo; Mumm rearrangement; unsymmetrical β-diacylamino

• esters, which enriches the studied content of fluoroalkyl diazo compounds. Results and Discussion Due to the instability of β-carbonyl diazo compounds and the occurrence of possible side reactions [58][59][60][61], screening of reaction conditions to optimize this conversion and inhibit the occurrence of

• ][40][41][58][59], a possible mechanism for this Cu-catalyzed reaction of β-trifluoromethyl β-amino esters was proposed in Scheme 4. Initially, β-trifluoromethyl β-amino ester 1a reacts with tert-butyl nitrite to form trifluoromethylated β-carbonyl diazo intermediate A. Then, the diazo intermediate A