PBr sub(3)-mediated unexpected reductive deoxygenation of alpha -aryl-pyridinemethanols: synthesis of arylmethylpyridines

PBr sub(3)-mediated unexpected reductive deoxygenation of alpha -aryl-pyridinemethanols: synthesis of arylmethylpyridines

PBr sub(3)-mediated reductive deoxygenation of alpha -aryl-pyridinemethanols to provide arylmethylpyridines is described, the alcohol substrate scope is explored, free radical trap TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) is introduced, and the hydrogen source of the methylene product is defined...

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Veröffentlicht in:Tetrahedron 2016-03, Vol.72 (12), p.1566-1572
Hauptverfasser: Nishigaya, Yosuke, Umei, Kentaro, Watanabe, Daisuke, Kohno, Yasushi, Seto, Shigeki
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols
Deoxygenation
Free radicals
Hydrogen
Methylene
Substrates
Synthesis
Tetrahedrons
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Zusammenfassung:PBr sub(3)-mediated reductive deoxygenation of alpha -aryl-pyridinemethanols to provide arylmethylpyridines is described, the alcohol substrate scope is explored, free radical trap TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) is introduced, and the hydrogen source of the methylene product is defined. The unexpected reaction enabled us to prepare previously inaccessible, novel EP sub(1) antagonists.
ISSN:0040-4020
DOI:10.1016/j.tet.2016.02.005