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4
Ar
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3
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Ag(I)
R
Cu(III)
Ar
Cu(III)
5
R
6
ArB(OH)2
2
Scheme 1. Possible mechanism.
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tive elimination of intermediate 6, giving the coupled product 3
and regenerating the active copper(I).
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In summary, we have successfully developed a copper-cata-
lyzed cross-coupling reaction of arylboronic acids with terminal al-
kynes, especially electron-poor analogue in moderate to good
yields.14 It represents a practical alternative for the Sonogashira
reaction. Compared with other transition-metal catalyst systems,
this protocol is simple and avoids the use of air-sensitive and/or
expensive catalysts.
12. Examples for synthesis of conjugated acetylenic carboxylates, see: (a) Stefani,
H. A.; Cella, R.; Doerr, F. A.; de Pereira, C. M. P.; Gomes, F. P.; Zeni, G.
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1991; (c) Böttcher, A.; Becker, H.; Brunner, M.; Preiss, T.; Henkelmann, J.; De
Acknowledgment
We thank the National Natural Science Foundation of China
(No. 20504023) for financial support.
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Supplementary data
Supplementary data associated with this article can be found, in
References and notes
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14. General procedure: Under air atmosphere, a reaction tube was charged with
arylboronic acid (0.25 mmol), alkyne (0.375 mmol), CuI (7.2 mg, 15 mol %),
Ag2O (115 mg, 0.5 mmol), Cs2CO3 (163 mg, 0.5 mmol), and DCE (2 mL). After
the mixture was heated at 80 °C for 36 h, the solvent was evaporated under
reduced pressure and the residue was purified by flash column
chromatography on a silica gel to give the product.
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