Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles

Antonio Arcadi; Massimiliano Aschi; Marco Chiarini; Giancarlo Fabrizi; Andrea Fochetti; Antonella Goggiamani; Federica Iavarone; Antonia Iazzetti; Andrea Serraiocco; Roberta Zoppoli

doi:10.1021/acsomega.4c02409

Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles

Antonio Arcadi
, Massimiliano Aschi
, Marco Chiarini
, Giancarlo Fabrizi^*
, Andrea Fochetti
, Antonella Goggiamani
, Federica Iavarone
, Antonia Iazzetti^*
, Andrea Serraiocco
, Roberta Zoppoli

^*Autore corrispondente per questo lavoro

University of L'Aquila
University of Teramo
Università di Roma

Risultato della ricerca: Contributo in rivista › Articolo

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 eta(3)-indolyl-palladium intermediate has been observed, and the selectivity control C1 '/C3 seems to depend on the nature of the protecting group and ligand. The reactivity of 3-indolylmethyl acetates has also been also investigated. Quantum chemical calculations support the experimental results.

Lingua originale	Inglese
pagine (da-a)	1-13
Numero di pagine	13
Rivista	ACS Omega
Numero di pubblicazione	June
DOI	https://doi.org/10.1021/acsomega.4c02409
Stato di pubblicazione	Pubblicato - 2024

All Science Journal Classification (ASJC) codes

Chimica Generale
Ingegneria Chimica Generale

Keywords

2- indolylmethyl acetates
indole-2-carbinol
indole-3-carbinol
palladium

Accesso al documento

10.1021/acsomega.4c02409

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title = "Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles",

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 eta(3)-indolyl-palladium intermediate has been observed, and the selectivity control C1 '/C3 seems to depend on the nature of the protecting group and ligand. The reactivity of 3-indolylmethyl acetates has also been also investigated. Quantum chemical calculations support the experimental results.",

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author = "Antonio Arcadi and Massimiliano Aschi and Marco Chiarini and Giancarlo Fabrizi and Andrea Fochetti and Antonella Goggiamani and Federica Iavarone and Antonia Iazzetti and Andrea Serraiocco and Roberta Zoppoli",

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doi = "10.1021/acsomega.4c02409",

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T1 - Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles

AU - Arcadi, Antonio

AU - Aschi, Massimiliano

AU - Chiarini, Marco

AU - Fabrizi, Giancarlo

AU - Fochetti, Andrea

AU - Goggiamani, Antonella

AU - Iavarone, Federica

AU - Iazzetti, Antonia

AU - Serraiocco, Andrea

AU - Zoppoli, Roberta

PY - 2024

Y1 - 2024

N2 - 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 eta(3)-indolyl-palladium intermediate has been observed, and the selectivity control C1 '/C3 seems to depend on the nature of the protecting group and ligand. The reactivity of 3-indolylmethyl acetates has also been also investigated. Quantum chemical calculations support the experimental results.

AB - 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 eta(3)-indolyl-palladium intermediate has been observed, and the selectivity control C1 '/C3 seems to depend on the nature of the protecting group and ligand. The reactivity of 3-indolylmethyl acetates has also been also investigated. Quantum chemical calculations support the experimental results.

KW - 2- indolylmethyl acetates

KW - indole-2-carbinol

KW - indole-3-carbinol

KW - palladium

KW - 2- indolylmethyl acetates

KW - indole-2-carbinol

KW - indole-3-carbinol

KW - palladium

UR - https://publicatt.unicatt.it/handle/10807/281917

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U2 - 10.1021/acsomega.4c02409

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JO - ACS Omega

JF - ACS Omega

IS - June

ER -

Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Accesso al documento

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