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

A novel route to 1,3-oxazaheterocycles based on cooperative Ru–H/Brønsted 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 Brønsted acid is responsible for generation of an electrophilic i...

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Bibliographic Details
Published in:Organic letters 2016-02, Vol.18 (4), p.642-645
Main Authors: Bernárdez, Rodrigo, Suárez, Jaime, Fañanás-Mastral, Martín, Varela, Jesús A, Saá, Carlos
Format: Article
Language:English
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Summary:A novel route to 1,3-oxazaheterocycles based on cooperative Ru–H/Brønsted 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 Brønsted 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03499