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N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide
CAS Number:
109032-22-6
Molecular Formula:
C13H12N2O6S
Tunable regiodivergent phosphine-catalyzed [3 + 2] cycloaddition of alkynones and trifluoroacetyl phenylamides
Literature Information
Publication Date
2017-08-29
DOI
10.1039/C7QO00512A
Impact Factor
5.281
Authors
Yao-Liang Sun, Yin Wei
View Original
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.
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Source Journal
Organic Chemistry Frontiers
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7.8
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