Oxirane synthesis from diazocarbonyl compounds via NHC-Ag+ catalysis

• Published in: Tetrahedron letters Vol. 55; no. 18; pp. 2969 - 2972
• Main Authors: Wang, Zhen, Wen, Jian, Bi, Qing-Wei, Xu, Xiao-Qi, Shen, Zhu-Qing, Li, Xiao-Xiao, Chen, Zili
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 30-04-2014
• Subjects: Carbene transfer reaction; N-Heterocyclic carbene silver complex; Oxirane synthesis; Silver carbenoid; Silver carbenoid; N-Heterocyclic carbene silver complex; Carbene transfer reaction; Oxirane synthesis
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2014.03.105

N-Heterocyclic carbene ligated silver catalyst was utilized to mediate [2+1] cycloaddition of diazo esters with aryl aldehydes to give oxirane derivatives. [Display omitted]
A new method was developed to synthesize oxirane products from the reaction of diazocarbonyl substrates with aryl aldehydes by using Ag(I) N-heterocyclic carbene complex as the catalyst. A combination of N-heterocyclic carbene silver complex (IPrAgCl) with another silver salt (AgOTf) generated the catalytic active IPr-Ag+ intermediate, which then catalyzed the epoxidation reaction.