Synthesis of highly functionalized biaryls by condensation of 2-fluoro-1,3-bis(silyloxy) 1,3-dienes with 3-cyanochromones and subsequent domino "retro-Michael/aldol/fragmentation".
The Me(3)SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/fragmentation" reaction.
Institut für Chemie der Universität Rostock, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany.
Muhammad Farooq
MF
Ibad
Obaid-ur-Rahman
OU
Abid
Muhammad
M
Adeel
Muhammad
M
Nawaz
Verena
V
Wolf
Alexander
A
Villinger
Peter
P
Langer
D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002867:Chromones; D011090:Polyenes