Fine Tuning of Quantum Dots Photocatalysts for the Synthesis of Tropane Alkaloid Skeletons.

Dabbous, Ali; Colson, Eloïse; Chakravorty, Debargha; Mouesca, Jean-Marie; Lombard, Christian; Caillat, Sylvain; Ravanat, Jean-Luc; Dubois, Fabien; Dénès, Fabrice; Renaud, Philippe; Maurel, Vincent (2023). Fine Tuning of Quantum Dots Photocatalysts for the Synthesis of Tropane Alkaloid Skeletons. Chemistry: a European journal, 29(28), e202300303. Wiley 10.1002/chem.202300303

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Several types of Quantum Dots (QDs) (CdS, CdSe and InP, as well as core-shell QDs such as type I InPZnS, quasi type-II CdSe-CdS and inverse type-I CdS-CdSe) were considered for generating α-aminoalkyl free radicals. The feasibility of the oxidation of the N-aryl amines and the generation of the desired radical was evidenced experimentally by quenching of the photoluminescence of the QDs and by testing a vinylation reaction using an alkenylsulfone radical trap. The QDs were tested in a radical [3+3]annulation reaction giving access to tropane skeletons and that requires the completion of two consecutive catalytic cycles. Several QDs such as CdS core, CdSe core and inverted type I CdS-CdSe core-shell proved to be efficient photocatalysts for this reaction. Interestingly, the addition of a second shorter chain ligand to the QDs appeared to be essential to complete the second catalytic cycle and to obtain the desired bicyclic tropane derivatives. Finally, the scope of the [3+3]-annulation reaction was explored for the best performing QDs and isolated yields that compares well with classical iridium photocatalysis were obtained.

Item Type:	Journal Article (Original Article)
Division/Institute:	08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)
UniBE Contributor:	Colson, Eloïse, Dénès, Fabrice Pierre François
Subjects:	500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry
ISSN:	1521-3765
Publisher:	Wiley
Language:	English
Submitter:	Pubmed Import
Date Deposited:	06 Mar 2023 12:47
Last Modified:	17 May 2023 00:14
Publisher DOI:	10.1002/chem.202300303
PubMed ID:	36867586
Uncontrolled Keywords:	Alkaloids Aminium free radicals Quantum dots Tropanes photoredox catalysis
URI:	https://boris.unibe.ch/id/eprint/179493