FeCl3-catalyzed synthesis of functionally diverse dibenzo[b,f]oxepines and benzo[b]oxepines via alkyne-aldehyde metathesis.
An efficient synthesis of dibenzo[b,f]oxepines and benzo[b]oxepines via FeCl3-catalyzed alkyne-aldehyde metathesis reaction is described. Structurally diverse dibenzo[b,f]oxepines and benzo[b]oxepines have been achieved in good yields with high regio- and chemoselectivity under mild conditions. Notably, among the various catalysts such as Fe(III), Au(III), In(III), Zn(II), Ag(I) and triflic acid, the alkyne-aldehyde metathesis reaction of 2-(2'-phenylethynyl-phenyloxy)-benzaldehyde is only catalyzed by environmentally friendly and sustainable iron(III) chloride.
Department of Chemistry, Jadavpur University, Kolkata-700 032, West Bengal, India. jumasish2004@yahoo.co.in.
Krishnendu
K
Bera
Swapnadeep
S
Jalal
Soumen
S
Sarkar
Umasish
U
Jana
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001584:Benzoxepins / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003990:Dibenzoxepins / Q000138:chemical synthesis* / Q000737:chemistry; D005290:Ferric Compounds / Q000737:chemistry*; D015394:Molecular Structure
D000447:Aldehydes; D000480:Alkynes; D001584:Benzoxepins; D002712:Chlorides; D003990:Dibenzoxepins; D005290:Ferric Compounds; C024555:ferric chloride