Original TDAE strategy using propargylic chloride: rapid access to 1,4-diarylbut-3-ynol derivatives.
We report herein the first synthesis of propargylic alcohols using an organic reducing agent. Diarylbutynol derivatives are formed in moderate to good yields under mild conditions from the reaction of 1-(3-chloroprop-1-ynyl)-4-nitrobenzene with various aromatic aldehydes using tetrakis(dimethylamino)ethylene (TDAE) as reductant.
Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Institut de Chimie Radicalaire ICR, UMR 7273, Aix-Marseille Univ, CNRS, 27 Boulevard Jean Moulin, 13385 Marseille Cedex 05, France.
Manon
M
Roche
Thierry
T
Terme
Patrice
P
Vanelle
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry*; D000440:Butanols / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D002712:Chlorides / Q000138:chemical synthesis* / Q000737:chemistry; D004123:Dimethylamines / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry
D000480:Alkynes; D001547:Benzaldehydes; D000440:Butanols; D002712:Chlorides; D004123:Dimethylamines; D005030:Ethylenes; D020005:Propanols; C028255:propargyl alcohol; C548965:tetrakis(dimethylamino)ethylene; C032175:benzaldehyde