Palladium-Catalyzed Tsuji–Trost-Type Reaction of 3-Indolylmethylacetates with O, and S Soft Nucleophiles

Iazzetti, Antonia; Arcadi, Antonio; Chiarini, Marco; Fabrizi, Giancarlo; Goggiamani, Antonella; Marrone, Federico; Serraiocco, Andrea; Zoppoli, Roberta

doi:10.3390/molecules29143434

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Open AccessArticle

Palladium-Catalyzed Tsuji–Trost-Type Reaction of 3-Indolylmethylacetates with O, and S Soft Nucleophiles

by

Antonia Iazzetti

^1,2,*

,

Antonio Arcadi

³

,

Marco Chiarini

⁴

,

Giancarlo Fabrizi

^5,*

,

Antonella Goggiamani

⁵

,

Federico Marrone

⁵

,

Andrea Serraiocco

⁵ and

Roberta Zoppoli

⁵

¹

Dipartimento di Scienze Biotecnologiche di Base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L. go Francesco Vito 1, 00168 Rome, RM, Italy

²

Policlinico Universitario ‘A. Gemelli’ Foundation-IRCCS, 00168 Rome, RM, Italy

³

Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi di L’Aquila, Via Vetoio, 67100 Coppito, AQ, Italy

⁴

Dipartimento di Bioscienze e Tecnologie Agro-Alimentari e Ambientali, Università di Teramo, via R. Balzarini, 64100 Teramo, TE, Italy

⁵

Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, RM, Italy

^*

Authors to whom correspondence should be addressed.

Molecules 2024, 29(14), 3434; https://doi.org/10.3390/molecules29143434

Submission received: 4 July 2024 / Revised: 17 July 2024 / Accepted: 19 July 2024 / Published: 22 July 2024

(This article belongs to the Special Issue New Metal Catalysts for Sustainable Chemistry)

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Abstract

The chemical valorization of widespread molecules in renewable sources is a field of research widely investigated in the last decades. In this context, we envisaged that indole-3-carbinol, present in different Cruciferae plants, could be a readily available building block for the synthesis of various classes of indoles through a palladium-catalyzed Tsuji–Trost-type reaction with O and S soft nucleophiles. The regiochemical outcome of this high-yielding functionalization shows that the nucleophilic substitution occurs only at the benzylic position. Interestingly, with this protocol, the sulfonyl unit could be appended to the indole nucleus, providing convenient access to new classes of molecules with potential bioactivity.

Keywords: 3-carbinol; Tsuji–Trost-type reaction; O and S soft nucleophiles; renewable sources

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MDPI and ACS Style

Iazzetti, A.; Arcadi, A.; Chiarini, M.; Fabrizi, G.; Goggiamani, A.; Marrone, F.; Serraiocco, A.; Zoppoli, R. Palladium-Catalyzed Tsuji–Trost-Type Reaction of 3-Indolylmethylacetates with O, and S Soft Nucleophiles. Molecules 2024, 29, 3434. https://doi.org/10.3390/molecules29143434

AMA Style

Iazzetti A, Arcadi A, Chiarini M, Fabrizi G, Goggiamani A, Marrone F, Serraiocco A, Zoppoli R. Palladium-Catalyzed Tsuji–Trost-Type Reaction of 3-Indolylmethylacetates with O, and S Soft Nucleophiles. Molecules. 2024; 29(14):3434. https://doi.org/10.3390/molecules29143434

Chicago/Turabian Style

Iazzetti, Antonia, Antonio Arcadi, Marco Chiarini, Giancarlo Fabrizi, Antonella Goggiamani, Federico Marrone, Andrea Serraiocco, and Roberta Zoppoli. 2024. "Palladium-Catalyzed Tsuji–Trost-Type Reaction of 3-Indolylmethylacetates with O, and S Soft Nucleophiles" Molecules 29, no. 14: 3434. https://doi.org/10.3390/molecules29143434

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Palladium-Catalyzed Tsuji–Trost-Type Reaction of 3-Indolylmethylacetates with O, and S Soft Nucleophiles

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