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Synlett 2000; 2000(7): 1061-1063
DOI: 10.1055/s-2000-6649
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Synthesis of Polycyclic Aromatic Hydrocarbons by Cocyclization of Arynes and Dimethyl Acetylenedicarboxylate (DMAD)

Diego Peña* , Dolores Pérez, Enrique Guitián, Luis Castedo
  • *Departamento de Quìmica Orgańica y Unidad Asociada al CSIC, Universidad de Santiago, 15706 Santiago de Compostela, Spain; Fax + 34 981 595012; E-mail: qoenrgui@usc.es
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Publication Date:
31 December 2000 (online)

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In a study of the palladium-catalyzed cocyclization of polycyclic arynes with DMAD, Pd2(dba)3 led selectively to cocyclization of one molecule of aryne and two molecules of DMAD, while Pd(PPh3)4 induced the cocyclization of two molecules of aryne with one molecule of DMAD. This allowed the selective preparation of several polycyclic aromatic hydrocarbons in good to excellent yield.

arynes - alkynes - cyclization - polycyclic aromatic compounds