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- W2977147369 endingPage "6829" @default.
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- W2977147369 abstract "DFT calculations of the AuCl 3 ‐catalyzed cycloisomerization of N ‐(propargyl)benzamide ( 1 ) have been conducted to reveal the detailed mechanism resulting in the bioactive 2,5‐disubstituted oxazole. A viable mechanism is established, featuring the co‐catalysis of the oxazoline‐AuCl 3 adduct. An oxazoline intermediate is afforded firstly by AuCl 3 coordination with 1 , 5‐ exo‐dig ‐cyclization, stepwise 1 ‐assisted protodeauration and coordination exchange. Once formed, the oxazoline species would replace 1 to assist the protodeauration, generating the oxazoline‐AuCl 3 adduct. In the last stage, significantly different from the simple deprotonation followed by protodeauration reported previously, the exo ‐cyclic C atom of the oxazoline accepts the adjacent allyl H atom of the oxazoline‐AuCl 3 to produce a zwitterionic intermediate, from which the allyl H atom of oxazoline fragment transfers to the allyl C atom of the adduct moiety, affording the final oxazole product and regenerating the oxazoline‐AuCl 3 . The present theoretical study provides new insight into the mechanism of the unusual cycloisomerization reaction." @default.
- W2977147369 created "2019-10-03" @default.
- W2977147369 creator A5003681868 @default.
- W2977147369 creator A5018814025 @default.
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- W2977147369 creator A5059317683 @default.
- W2977147369 creator A5068083147 @default.
- W2977147369 creator A5088173549 @default.
- W2977147369 date "2019-10-22" @default.
- W2977147369 modified "2023-09-25" @default.
- W2977147369 title "Mechanistic Investigation of Au(III)-Catalyzed Cycloisomerizations of <i>N</i> -Propargylcarboxamides" @default.
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