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Triazole-Au(I) complex as chemoselective catalyst in promoting propargyl ester rearrangements.

ABSTRACT: Triazole-Au (TA-Au) catalysts were employed in several transformations involving propargyl ester rearrangement. Good chemoselectivity was observed, which allowed the effective activation of the alkyne without affecting the reactivity of the allene ester intermediates. These results led to the investigation of the preparation of allene ester intermediates with TA-Au catalysts under anhydrous conditions. As expected, the desired 3,3-rearrangement products were obtained in excellent yields (generally >90% yields with 1% loading). Besides the typical ester migrating groups, carbonates and carbamates were also found to be suitable for this transformation, which provided a highly efficient, practical method for the preparation of substituted allenes.

SUBMITTER: Wang D

PROVIDER: S-EPMC3167893 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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Triazole-Au(I) complex as chemoselective catalyst in promoting propargyl ester rearrangements.

Wang Dawei D Zhang Yanwei Y Cai Rong R Shi Xiaodong X

Beilstein journal of organic chemistry 20110725

Triazole-Au (TA-Au) catalysts were employed in several transformations involving propargyl ester rearrangement. Good chemoselectivity was observed, which allowed the effective activation of the alkyne without affecting the reactivity of the allene ester intermediates. These results led to the investigation of the preparation of allene ester intermediates with TA-Au catalysts under anhydrous conditions. As expected, the desired 3,3-rearrangement products were obtained in excellent yields (general ...[more]

PMID: 21915202

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