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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| Published in | Tetrahedron Vol. 72; no. 48; pp. 7875 - 7887 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
01.12.2016
Elsevier |
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| Online Access | Get full text |
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| Abstract | 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.
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| AbstractList | Under basic conditions aryl halides can undergo S(RN)1 reactions, BHAS reactions and benzyne formations. Appropriate complex substrates afford an opportunity to study inherent selectivities. S(RN)1 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. 2016 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license. 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] |
| Author | Emery, Katie J. Tuttle, Tell Kennedy, Alan R. Murphy, John A. |
| Author_xml | – sequence: 1 givenname: Katie J. surname: Emery fullname: Emery, Katie J. – sequence: 2 givenname: Tell surname: Tuttle fullname: Tuttle, Tell email: tell.tuttle@strath.ac.uk – sequence: 3 givenname: Alan R. surname: Kennedy fullname: Kennedy, Alan R. – sequence: 4 givenname: John A. surname: Murphy fullname: Murphy, John A. email: john.murphy@strath.ac.uk |
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| Keywords | 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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| SSID | ssj0001123 |
| Score | 2.3323698 |
| Snippet | Under basic conditions aryl halides can undergo SRN1 reactions, BHAS reactions and benzyne formations. Appropriate complex substrates afford an opportunity to... Under basic conditions aryl halides can undergo S(RN)1 reactions, BHAS reactions and benzyne formations. Appropriate complex substrates afford an opportunity... |
| Source | Web of Science |
| SourceID | crossref webofscience elsevier |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 7875 |
| SubjectTerms | BHAS Chemistry Chemistry, Organic Coupling Electron transfer Physical Sciences Radical Science & Technology SRN1 |
| Title | C–C bond-forming reactions of ground-state aryl halides under reductive activation |
| URI | https://dx.doi.org/10.1016/j.tet.2016.05.083 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000388781600028 |
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