Palladium-Catalyzed Synthesis of 6-aryl Dopamine Derivatives

Calcaterra, Andrea; Fernández García, Santiago; Marrone, Federico; Bernini, Roberta; Fabrizi, Giancarlo; Goggiamani, Antonella; Iazzetti, Antonia

doi:10.3390/catal14070401

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Palladium-Catalyzed Synthesis of 6-aryl Dopamine Derivatives

by

Andrea Calcaterra

¹

,

Santiago Fernández García

¹

,

Federico Marrone

¹,

Roberta Bernini

^2,*

,

Giancarlo Fabrizi

^1,*

,

Antonella Goggiamani

¹

and

Antonia Iazzetti

^3,4

¹

Department of Chemistry and Technology of Drugs, Sapienza—University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy

²

Department of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via San Camillo de Lellis, 01100 Viterbo, Italy

³

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

⁴

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

^*

Authors to whom correspondence should be addressed.

Catalysts 2024, 14(7), 401; https://0-doi-org.brum.beds.ac.uk/10.3390/catal14070401

Submission received: 6 June 2024 / Revised: 21 June 2024 / Accepted: 22 June 2024 / Published: 25 June 2024

(This article belongs to the Section Catalytic Materials)

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Abstract

Dopamine is a key neurotransmitter involved in a series of biologically relevant processes and its derivatives have sparked significant interest as intriguing synthetic targets. This class of compounds is indeed not only considerable for the potential biological activities but is also promising for diverse applications in material science. In light of this, our research was focused on the synthesis of 6-aryldopamine derivatives starting from 4-(2-aminoethyl)phenol through a sequential protocol, whose main steps are hydroxylation, halogenation, and Suzuki cross-coupling. Our method demonstrated versatility, efficiency, and compatibility with various functional groups, including aldehydes, ketones, esters, ethers, and fluorine.

Keywords: dopamine; palladium-catalyzed synthesis; Suzuki reaction; dopamine derivatives; regioselective hydroxylation; catechol; regioselective aromatic chlorination

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MDPI and ACS Style

Calcaterra, A.; Fernández García, S.; Marrone, F.; Bernini, R.; Fabrizi, G.; Goggiamani, A.; Iazzetti, A. Palladium-Catalyzed Synthesis of 6-aryl Dopamine Derivatives. Catalysts 2024, 14, 401. https://0-doi-org.brum.beds.ac.uk/10.3390/catal14070401

AMA Style

Calcaterra A, Fernández García S, Marrone F, Bernini R, Fabrizi G, Goggiamani A, Iazzetti A. Palladium-Catalyzed Synthesis of 6-aryl Dopamine Derivatives. Catalysts. 2024; 14(7):401. https://0-doi-org.brum.beds.ac.uk/10.3390/catal14070401

Chicago/Turabian Style

Calcaterra, Andrea, Santiago Fernández García, Federico Marrone, Roberta Bernini, Giancarlo Fabrizi, Antonella Goggiamani, and Antonia Iazzetti. 2024. "Palladium-Catalyzed Synthesis of 6-aryl Dopamine Derivatives" Catalysts 14, no. 7: 401. https://0-doi-org.brum.beds.ac.uk/10.3390/catal14070401

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

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Palladium-Catalyzed Synthesis of 6-aryl Dopamine Derivatives

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