n -Bu 4 NI/K 2 S 2 O 8 Mediated Csp 2 -Csp 2 Bond Cleavage - Transformylation from p -Anisaldehyde to Primary Amides.

Autor: Liu X; Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Queens, New York 11367, United States.; Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, 365 Fifth Ave., New York, New York 10016, United States., Hee S; Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Queens, New York 11367, United States.; Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, 365 Fifth Ave., New York, New York 10016, United States., Sapir NG; Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Queens, New York 11367, United States., Li A; Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Queens, New York 11367, United States., Liu J; Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Queens, New York 11367, United States.; Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, 365 Fifth Ave., New York, New York 10016, United States., Chen Y; Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Queens, New York 11367, United States.; Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, 365 Fifth Ave., New York, New York 10016, United States.
Jazyk: angličtina
Zdroj: Advanced synthesis & catalysis [Adv Synth Catal] 2024 Jun 10; Vol. 366 (11), pp. 2489-2494. Date of Electronic Publication: 2024 Apr 09.
DOI: 10.1002/adsc.202301505
Abstrakt: n -Bu 4 NI/K 2 S 2 O 8 mediated transformylation from p -anisaldehyde to primary amides is reported. The mechanistic studies suggest the reaction occurs via a single electron transfer pathway. Based on the DFT electronic structure calculations of various reaction pathways, the most plausible mechanism involves the formation of a phenyl radical cation and an arenium ion as the key intermediates. It represents the first example where p -anisaldehyde is employed as a formyl source via a non-metal mediated Csp 2 -Csp 2 bond cleavage.
Databáze: MEDLINE
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