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

^*Corresponding author

University of L'Aquila
University of Teramo
Università di Roma

Research output: Contribution to journal › Article

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.

Original language	English
Pages (from-to)	1-13
Number of pages	13
Journal	ACS Omega
Issue number	June
DOIs	https://doi.org/10.1021/acsomega.4c02409
Publication status	Published - 2024

All Science Journal Classification (ASJC) codes

General Chemistry
General Chemical Engineering

Keywords

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

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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.",

keywords = "2- indolylmethyl acetates, indole-2-carbinol, indole-3-carbinol, palladium, 2- indolylmethyl acetates, indole-2-carbinol, indole-3-carbinol, palladium",

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",

year = "2024",

doi = "10.1021/acsomega.4c02409",

language = "English",

pages = "1--13",

journal = "ACS Omega",

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publisher = "American Chemical Society",

number = "June",

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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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UR - https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85196718905&origin=inward

U2 - 10.1021/acsomega.4c02409

DO - 10.1021/acsomega.4c02409

M3 - Article

SN - 2470-1343

SP - 1

EP - 13

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

Access to Document

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