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 language | English (US) |
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Pages (from-to) | 248-252 |
Number of pages | 5 |
Journal | Organic Chemistry Frontiers |
Volume | 2 |
Issue number | 3 |
DOIs | |
State | Published - Mar 2015 |
Bibliographical note
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