Issue 3, 2015

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
12 dec 2014
Accepted
10 jan 2015
First published
29 jan 2015

Org. Chem. Front., 2015,2, 248-252

Author version available

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

L. Peng, F. Xu, K. Shinohara, T. Nishida, K. Wakamatsu, A. Orita and J. Otera, Org. Chem. Front., 2015, 2, 248 DOI: 10.1039/C4QO00325J

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