Formation of the corannulene core by nickel-mediated intramolecular coupling of benzyl and benzylidene bromides: a versatile synthesis of dimethyl 1,2-corannulene dicarboxylate.
[reaction: see text] A practical synthesis of dimethyl 1,2-corannulene dicarboxylate (5) is reported, with the final ring-forming step achieved by the double intramolecular nickel powder mediated coupling of benzyl and benzylidene bromide groups with 60% isolated yield.
Sygula
Andrzej
A
Department of Chemistry and Ames Laboratory, Iowa State University, Ames 50011, USA. asygula@iastate.edu
Karlen
Steven D
SD
Sygula
Renata
R
Rabideau
Peter W
PW
D001593:Benzyl Compounds / Q000737:chemistry; D001597:Benzylidene Compounds / Q000737:chemistry; D003500:Cyclization; D009532:Nickel / Q000737:chemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*
D001593:Benzyl Compounds; D001597:Benzylidene Compounds; D011084:Polycyclic Aromatic Hydrocarbons; C434863:corannulene; C471503:dimethyl 1,2-corannulene dicarboxylate; D009532:Nickel; C038682:benzyl bromide