Remarkable electron-withdrawing effect of the Ph2P(O)-ethynyl group: Ph2P(O)-ethynyl-substituted aryl halides and copper acetylides for tailor-made Sonogashira couplings

Lifen Peng, Feng Xu, Kenta Shinohara, Takanori Nishida, Kan Wakamatsu, Akihiro Orita, Junzo Otera

Research output: Contribution to journalArticlepeer-review

10 Scopus citations


The electronic effect of the Ph2P(O)-ethynyl group in Sonogashira couplings was investigated. Ph2P(O)-ethynylphenyl iodide showed higher reactivity than diiodobenzene because of the electron-withdrawing effect of the Ph2P(O) group. Copper acetylide, which was prepared in situ from Ph2P(O)-ethyne, exhibited poor nucleophilicity and reacted with aryl iodides in Sonogashira couplings, but did not react with aryl bromides. This high selectivity enabled practical syntheses of a cyclic phenyleneethynylene and unsymmetrically substituted 9,10-bis(ethynyl)anthracenes.

Original languageEnglish (US)
Pages (from-to)248-252
Number of pages5
JournalOrganic Chemistry Frontiers
Issue number3
StatePublished - Mar 2015

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