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

Zhenhua Gu; K. Peter C. Vollhardt

doi:10.1055/s-0033-1338500

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(17): 2469-2473
DOI: 10.1055/s-0033-1338500

paper

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

Zhenhua Gu

Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA Fax: +1(510)6435208 eMail: kpcv@berkeley.edu

,

K. Peter C. Vollhardt*

Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA Fax: +1(510)6435208 eMail: kpcv@berkeley.edu

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Abstract

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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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Referenzen

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