Benzannulation via ruthenium-catalyzed diol-diene [4+2] cycloaddition: one- and two-directional syntheses of fluoranthenes and acenes.
A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol-diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol and tetraol reactants, benzannulation can be conducted efficiently in one- and two-directional modes, respectively, as illustrated in the construction of substituted fluoranthenes and acenes.
Department of Chemistry and Biochemistry, University of Texas at Austin , Austin, Texas 78712, United States.
Laina M
LM
Geary
Te-Yu
TY
Chen
T Patrick
TP
Montgomery
Michael J
MJ
Krische
D002384:Catalysis; D061565:Cycloaddition Reaction; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
D005449:Fluorenes; C007738:fluoranthene; D012428:Ruthenium