Radical-mediated intramolecular C–C bond formation and the deoxygenation of alcohols under solvent-free conditions with tributyl methyl ammonium hypophosphite

Radical-mediated intramolecular C–C bond formation and the deoxygenation of alcohols under solvent-free conditions with tributyl methyl ammonium hypophosphite

A green, solvent-free protocol was developed for the radical-mediated intramolecular cyclization of haloacetals and the deoxygenation of S-methyl dithiocarbonates and cyclic thionocarbonate. This process uses tributyl methyl ammonium hypophosphite as a H-donor in the presence of triethylborane or t-...

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Veröffentlicht in:Tetrahedron letters 2011-12, Vol.52 (51), p.6927-6929
Hauptverfasser: Lee, Eun Hwa, Cho, Dae Hyan, Satyender, Apuri, Jang, Doo Ok
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols
Bonding
Carbon-carbon composites
Chemistry
C–C bond formation
Deoxygenation
Exact sciences and technology
Free radicals chemistry
Methodology
Organic chemistry
Peroxides
Radical reaction
Reactivity and mechanisms
Solvent-free
Tetrahedrons
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Beschreibung
Zusammenfassung:A green, solvent-free protocol was developed for the radical-mediated intramolecular cyclization of haloacetals and the deoxygenation of S-methyl dithiocarbonates and cyclic thionocarbonate. This process uses tributyl methyl ammonium hypophosphite as a H-donor in the presence of triethylborane or t-butyl peroxide. This methodology provides eco-friendly reaction conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.10.063