Copper-catalyzed formal [4 + 2] annulation between alkyne and fullerene bromide.
A copper-catalyzed reaction of arylacetylene or enyne with C(60)Ar(5)Br effects a formal [4 + 2] annulation reaction to form a dihydronaphthalene ring fused to the fullerene core. The reaction involves a formal C-H bond activation and takes place by a copper-mediated radical mechanism. This reaction takes place in 60-75% overall yield from [60]fullerene and creates axial chirality in the product because of restricted rotation of the top aryl groups.
Xiao
Zuo
Z
Nakamura Functional Carbon Cluster Project, ERATO, Japan Science and Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Matsuo
Yutaka
Y
Nakamura
Eiichi
E
D000480:Alkynes / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D037741:Fullerenes / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D001965:Bromides; D037741:Fullerenes; D009281:Naphthalenes; D003300:Copper