Phenylated Benzotetraphenes (Dibenzanthracenes) by Nickel-Catalyzed Diphenylacetylene Cycloadditions to Linear [3]Phenylenes

Abstract

Ni(COD)(PMe₃)₂ catalyzes the cycloaddition of diphenylacetylene to the four-membered rings of linear [3]phenylene and its 2,3,7,8-tetrakis(trimethylsilyl) derivative. The reaction proceeds via initial formation of the 5,6-diphenylbenzo[3,4]cyclobuta[1,2-b]phenanthrene frame, followed by a competitive second, nonregio­selective alkyne insertion to furnish the corresponding phenyl-­substituted benzo[k]- and -[m]tetraphenes.

Key words

alkynes - arenes - cycloaddition - nickel - polycycles

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