Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)(3)/Bronsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles

ORGANIC LETTERS

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Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)(3)/Bronsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles

Abstract: A novel route to 1,3-oxazaheterocycles based on cooperative RuH/Bronsted acid catalysis is reported. The use of the commercially available RuH2(CO)(PPh3)(3) complex allows for an efficient long distance chain-walking process while the Bronsted acid is responsible for generation of an electrophilic iminium ion which is trapped intramolecularly by an alcohol moiety. The alcohol, besides its nucleophilic function, also plays an important role in the stabilization of the Ru catalyst.

Author(s): Bernardez, R; Suarez, J; Fananas-Mastral, M; Varela, JA; Saa, C

ORGANIC LETTERS

Volume: 18 Pages: 642-645 Published: FEB 19 2016

PDF: Tandem Long Distance Chain-Walking Cyclization via RuH2 CO PPh3 3 Bronsted Acid Catalysis Entry to Aromatic Oxazaheterocycles

DOI: 10.1021/acs.orglett.5b03499

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O Laboratório Aberto de Interatividade para Disseminação do Conhecimento Científico e Tecnológico (LAbI), vinculado à Universidade Federal de São Carlos (UFSCar), é voltado à prática da divulgação científica pautada na interatividade; nas relações entre Ciência, Arte e Tecnologia.