Deprotonation of benzylic ethers using a hindered phosphazene base. A synthesis of benzofurans from ortho-substituted benzaldehydes.
The hindered nonionic phosphazene base P(4)-t-Bu efficiently deprotonates o-arylmethoxy benzaldehydes, leading to a direct synthesis of benzofurans. Strong ionic bases such as LDA, LiTMP, and KH failed.
Kraus
G A
GA
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA. jverkade@iastate.edu
Zhang
N
N
Verkade
J G
JG
Nagarajan
M
M
Kisanga
P B
PB
D001547:Benzaldehydes; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D009943:Organophosphorus Compounds
D001547:Benzaldehydes; D001572:Benzofurans; D007202:Indicators and Reagents; D009943:Organophosphorus Compounds