The palladium-catalyzed reaction of N-protected 2-indolylmethyl acetates with soft carbon pronucleophiles is described. Besides the formation of the expected coupling reaction at the C1′position, unprecedented attack at the C3 position of the plausible η3-indolyl-palladium intermediate has been observed, and the selectivity control C1′/C3 seems to depend on the nature of the protecting groupand ligand. The reactivity of 3-indolylmethyl acetates has also been also investigated. Quantum chemical calculations support the experimental results.
Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles.
Antonio ArcadiMembro del Collaboration Group
;Massimiliano AschiMembro del Collaboration Group
;Marco ChiariniMembro del Collaboration Group
;
2024-01-01
Abstract
The palladium-catalyzed reaction of N-protected 2-indolylmethyl acetates with soft carbon pronucleophiles is described. Besides the formation of the expected coupling reaction at the C1′position, unprecedented attack at the C3 position of the plausible η3-indolyl-palladium intermediate has been observed, and the selectivity control C1′/C3 seems to depend on the nature of the protecting groupand ligand. The reactivity of 3-indolylmethyl acetates has also been also investigated. Quantum chemical calculations support the experimental results.File in questo prodotto:
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