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Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763-1766. For another gold-catalyzed transformation of alkynylamides, see: Couty, S.; Meyer, C. Cossy, J. Angew. Chem., Int. Ed. 2006, 45, 6726-6730.
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The reaction reported by Hashmi and coworkers (ref 16) was limited to the use of substrates 3 bearing a hydrogen or a silyl group on the akyne and another electron-withdrawing group Boc
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The reaction reported by Hashmi and coworkers (ref 16) was limited to the use of substrates 3 bearing a hydrogen or a silyl group on the akyne and another electron-withdrawing group (Boc, Ts, Piv) on the nitrogen atom.
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Ts, Piv) on the nitrogen atom
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53
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The poor yields obtained in the case of 3e and 3h may be attributed to a greater steric hindrance around the nitrogen center.
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The poor yields obtained in the case of 3e and 3h may be attributed to a greater steric hindrance around the nitrogen center.
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Mezailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133-4136.
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6) did promote the reaction (53%, 64%) but their efficiency proved limited to a few substrates (see eqs 1 and 2).
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6) did promote the reaction (53%, 64%) but their efficiency proved limited to a few substrates (see eqs 1 and 2).
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1H NMR on the crude reaction mixture.
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1H NMR on the crude reaction mixture.
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