Palladium-catalyzed C–H alkenylation of quinoxaline N-oxide enabled by a mono-N-protected amino acid. Issue 26 (27th June 2018)

• Record Type: Journal Article
• Authors: Freire Franco, Márcia Silvana; de Paula, Murilo Helder; Glowacka, Paulina Cecylia; Fumagalli, Fernando; Clososki, Giuliano Cesar; da Silva Emery, Flavio
• Is Part Of: Tetrahedron letters. Volume 59:Issue 26(2018)
• Page Start: 2562
• Page End: 2566
• Publication Date: 2018-06-27
• Subjects: C–H activation -- Quinoxaline -- Palladium -- Alkenylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.05.054
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Novel styrylquinoxaline- N -oxides synthesized via palladium(II) C–H activation reaction. Pivotal influence of mono- N -protected amino acid in this Fujiwara-Moritani reaction. Mechanistic implications using mono- N -protected amino acid as the ligand. Post modification to obtain the deoxygenated styrylquinoxaline derivatives. Abstract: The efficient alkenylation of quinoxaline N -oxide was achieved via Pd-catalyzed C–H activation, using the assistance of a mono- N -protected amino acid. Further deoxygenation of the 2-styrylquinoxaline- N -oxides yielded the corresponding styrylquinoxaline derivatives.