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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.

SUBMITTER: Bellotti P

PROVIDER: S-EPMC8179282 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Three-component three-bond forming cascade <i>via</i> palladium photoredox catalysis.

Bellotti Peter P Koy Maximilian M Gutheil Christian C Heuvel Steffen S Glorius Frank F

Chemical science 20201207 5

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 f ...[more]

PMID: 34163944

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