C–C bond-forming reactions of ground-state aryl halides under reductive activation

Under basic conditions aryl halides can undergo SRN1 reactions, BHAS reactions and benzyne formations. Appropriate complex substrates afford an opportunity to study inherent selectivities. SRN1 reactions are usually favoured under photoactivated conditions, but this paper reports their success using...

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Bibliographic Details
Published inTetrahedron Vol. 72; no. 48; pp. 7875 - 7887
Main Authors Emery, Katie J., Tuttle, Tell, Kennedy, Alan R., Murphy, John A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.12.2016
Elsevier
Subjects
BHAS
Chemistry
Chemistry, Organic
Coupling
Electron transfer
Physical Sciences
Radical
Science & Technology
SRN1
Electron transfer
Coupling
SRN1
Radical
BHAS
ROOM-TEMPERATURE
INTRAMOLECULAR ARYLATION
S(RN)1
FREE COUPLING REACTIONS
MEDIATED SYNTHESIS
POTASSIUM TERT-BUTOXIDE
UNACTIVATED ARENES
TRANSITION-METALS
HOMOLYTIC AROMATIC-SUBSTITUTION
ELECTRON-TRANSFER
H-ARYLATION
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Summary:Under basic conditions aryl halides can undergo SRN1 reactions, BHAS reactions and benzyne formations. Appropriate complex substrates afford an opportunity to study inherent selectivities. SRN1 reactions are usually favoured under photoactivated conditions, but this paper reports their success using ground-state and transition metal-free conditions. In benzene, the enolate salt 12, derived by deprotonation of diketopiperazine 11, behaves as an electron donor, and assists the initiation of the reactions, but in DMSO, it is not required. The outcomes are compared and contrasted with a recent photochemical study on similar substrates. A particular difference is the prevalence of hydride shuttle reactions under relatively mild thermal conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.05.083