Dihalo-substituted dibenzopentalenes: Their practical synthesis and transformation to dibenzopentalene derivatives

Feng Xu, Lifen Peng, Akihiro Orita, Junzo Otera

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

Diiodo- and bromo, iodo-substituted dibenzopentalenes were obtained by treatment of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene with I 2 and IBr, respectively. These dihalo-substituted pentalenes reacted with terminal ethynes in Sonogashira coupling and with arylboronic acid in Suzuki-Miyaura coupling to give a series of phenylethynyl- and/or aryl-substituted pentalenes. Suzuki-Miyaura coupling of the halopentalenes with in situ prepared pentaleneboronic esters provided bis-, tri-, and tetra(dibenzopentalene)s. It was found that these dibenzopentalene oligomers underwent facile electrochemical reduction and exhibited a bathochromic shift in UV-vis absorption spectra because of their expanded π-systems.

Original languageEnglish (US)
Pages (from-to)3970-3973
Number of pages4
JournalOrganic Letters
Volume14
Issue number15
DOIs
StatePublished - Aug 3 2012

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