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 journalArticle

9 Scopus citations

Abstract

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
Volume2
Issue number3
DOIs
StatePublished - Mar 2015

Fingerprint Dive into the research topics of 'Remarkable electron-withdrawing effect of the Ph<sub>2</sub>P(O)-ethynyl group: Ph<sub>2</sub>P(O)-ethynyl-substituted aryl halides and copper acetylides for tailor-made Sonogashira couplings'. Together they form a unique fingerprint.

  • Cite this