Biomaterial Database

Copper-catalyzed formal [4 + 2] annulation between alkyne and fullerene bromide. 2010

Zuo Xiao, and Yutaka Matsuo, and Eiichi Nakamura

Nakamura Functional Carbon Cluster Project, ERATO, Japan Science and Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

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.

UI	MeSH Term	Description	Entries
D009281	Naphthalenes	Two-ring crystalline hydrocarbons isolated from coal tar. They are used as intermediates in chemical synthesis, as insect repellents, fungicides, lubricants, preservatives, and, formerly, as topical antiseptics.
D001965	Bromides	Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Bromide
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D003300	Copper	A heavy metal trace element with the atomic symbol Cu, atomic number 29, and atomic weight 63.55.	Copper-63,Copper 63
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D000480	Alkynes	Hydrocarbons with at least one triple bond in the linear portion, of the general formula Cn-H2n-2.	Acetylenic Compounds,Alkyne,Acetylenes
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D037741	Fullerenes	A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.	Buckyballs,Buckminsterfullerenes,Buckminsterfullerene,Buckyball,Fullerene