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Tunable regiodivergent phosphine-catalyzed [3 + 2] cycloaddition of alkynones and trifluoroacetyl phenylamides

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Abstract

Alkynones can be activated by phosphine as a nucleophilic catalyst, and then trapped by a series of trifluoroacetyl phenylamides to afford cycloaddition products. Through subtly adjusting the substituent of trifluoroacetyl phenylamides, the addition of water and changing the reaction temperature, two kinds of highly regioselective cycloaddition products were obtained in moderate to excellent yields. Plausible mechanisms were proposed and supported by the deuterium-labeling experiments and DFT calculations. DFT calculations demonstrate that the currently accepted intramolecular proton transfer processes involved in these reactions are impossible, and these proton transfer processes can proceed with the assistance of substrates containing an acidic moiety or by the addition of water. Our mechanistic studies provide reasonable explanations for the regioselectivity affected by the protic additive H2O, and the reaction temperature.

Graphical abstract: Tunable regiodivergent phosphine-catalyzed [3 + 2] cycloaddition of alkynones and trifluoroacetyl phenylamides

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Publication details

The article was received on 26 Jun 2017, accepted on 28 Aug 2017 and first published on 29 Aug 2017


Article type: Research Article
DOI: 10.1039/C7QO00512A
Citation: Org. Chem. Front., 2017, Advance Article
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    Tunable regiodivergent phosphine-catalyzed [3 + 2] cycloaddition of alkynones and trifluoroacetyl phenylamides

    Y. Sun, Y. Wei and M. Shi, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00512A

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