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- W2895740249 abstract "A regioselective heterocyclization–Sonogashira coupling cascade between 2-alkynylbenzamides and terminal alkynes is described. The reaction proceeds under Pd(II) catalysis, with air used as a terminal oxidant to regenerate the catalyst from the Pd(0) produced in the C–C coupling. The cascade process provides alkynyl-substituted isobenzofuranimine products in a single operation. These products are the result of a 5-exo O-cyclization, while products derived from the alternative 6-endo cyclization mode are observed in minor amounts. Two competing mechanisms have been considered to account for the observed results. Both involve heterocyclization, alkyne C–H activation, and reductive elimination steps but differ in the relative order of the first two. Control experiments using a preformed alkynylpalladium complex have shown that a mechanism starting with alkyne C–H activation is viable. On the other hand, DFT calculations indicate that the alternative cyclization-first mechanism is also competitive, particular..." @default.
- W2895740249 created "2018-10-12" @default.
- W2895740249 creator A5012131514 @default.
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- W2895740249 date "2018-10-01" @default.
- W2895740249 modified "2023-10-17" @default.
- W2895740249 title "Regioselective Palladium-Catalyzed Heterocyclization–Sonogashira Coupling Cascades from 2-Alkynylbenzamides and Terminal Alkynes: Experimental and DFT Studies" @default.
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- W2895740249 doi "https://doi.org/10.1021/acs.organomet.8b00519" @default.
- W2895740249 hasPublicationYear "2018" @default.
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