Issue 5, 2021

Three-component three-bond forming cascade via palladium photoredox catalysis

Abstract

A highly modular radical cascade strategy based upon radical cyclisation/allylic substitution sequence between alkyl/aryl bromides, 1,3-dienes and nucleophiles ranging from sulfinates to amines, phenols and 1,3-dicarbonyls is described (>80 examples). Palladium phosphine complexes – which merge properties of photo- and cross coupling-catalysts – allow to forge three bonds with complete 1,4-selectivity and stereocontrol, delivering highly value added carbocyclic and heterocyclic motifs that can feature – inter alia – vicinal quaternary centers, free protic groups, gem-difluoro motifs and strained rings. Furthermore, a flow chemistry approach was for the first time applied in palladium–photocatalysed endeavors involving radicals.

Graphical abstract: Three-component three-bond forming cascade via palladium photoredox catalysis

Supplementary files

Article information

Article type
Edge Article
Submitted
07 oct. 2020
Accepted
06 déc. 2020
First published
07 déc. 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 1810-1817

Three-component three-bond forming cascade via palladium photoredox catalysis

P. Bellotti, M. Koy, C. Gutheil, S. Heuvel and F. Glorius, Chem. Sci., 2021, 12, 1810 DOI: 10.1039/D0SC05551D

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