A regioselective vinylation of aromatic and aliphatic aldehydes promoted by the merging of photoredox and nickel catalysis is here reported. A comprehensive investigation on the reaction conditions allowed the disclosure of a valid and reproducible protocol based on a nickel-mediated reductive coupling approach under visible light irradiation. The employment of 3CzClIPN (2,4,6-tris(carbazol-9-yl)-5-chloro-isophthalonitrile) as the photocatalyst and Hantzsch's ester as the sacrificial organic reductant replace the use of boron-, silicon- or zinc-based reducing agents, making this method a worthy alternative to the already known protocols. The developed mild reaction conditions allow the access to a wide range of substituents decorating both the aldehyde and the alkyne. Moreover, careful photophysical investigations shed light on the mechanism of the reaction.

Dual Photoredox and Nickel Catalysed Reductive Coupling of Alkynes and Aldehydes / F. Calogero, G. Magagnano, S. Potenti, A. Gualandi, A. Fermi, P. Ceroni, P.G. Cozzi. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 364:19(2022 Oct 04), pp. 3410-3419. [10.1002/adsc.202200589]

Dual Photoredox and Nickel Catalysed Reductive Coupling of Alkynes and Aldehydes

F. Calogero
Co-primo
;
S. Potenti
Co-primo
;
2022

Abstract

A regioselective vinylation of aromatic and aliphatic aldehydes promoted by the merging of photoredox and nickel catalysis is here reported. A comprehensive investigation on the reaction conditions allowed the disclosure of a valid and reproducible protocol based on a nickel-mediated reductive coupling approach under visible light irradiation. The employment of 3CzClIPN (2,4,6-tris(carbazol-9-yl)-5-chloro-isophthalonitrile) as the photocatalyst and Hantzsch's ester as the sacrificial organic reductant replace the use of boron-, silicon- or zinc-based reducing agents, making this method a worthy alternative to the already known protocols. The developed mild reaction conditions allow the access to a wide range of substituents decorating both the aldehyde and the alkyne. Moreover, careful photophysical investigations shed light on the mechanism of the reaction.
Aldehydes; Metallaphotoredox catalysis; Nickel catalysis; Regioselectivity; Vinylation;
Settore CHIM/06 - Chimica Organica
   Raising up Catalysis for Innovative Developments (SURSUMCAT)
   SURSUMCAT
   MINISTERO DELL'ISTRUZIONE E DEL MERITO
   20174SYJAF_002

   Straightening training, research and innovation capacities in the valorization of bio-renewable resource
   Biomass4Synthons
   European Commission
   Horizon 2020 Framework Programme
   951996
4-ott-2022
30-giu-2022
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/1018268
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