Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes
Enolates derived from α-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd 2(dba) 3 and the ligand DPEphos effects the key bond formation to del...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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2006
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| _version_ | 1797070226011979776 |
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| author | Willis, M Taylor, D Gillmore, A |
| author_facet | Willis, M Taylor, D Gillmore, A |
| author_sort | Willis, M |
| collection | OXFORD |
| description | Enolates derived from α-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd 2(dba) 3 and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C-S bond formation using identical reaction conditions and are converted to benzothiophene products. A cascade sequence that produces the required α-aryl ketones in situ has also been developed, although the substrate scope is more restricted. © 2006 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-06T22:35:52Z |
| format | Journal article |
| id | oxford-uuid:59df51c3-7048-4f5e-818f-fd037113fb86 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:35:52Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:59df51c3-7048-4f5e-818f-fd037113fb862022-03-26T17:12:18ZPalladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:59df51c3-7048-4f5e-818f-fd037113fb86EnglishSymplectic Elements at Oxford2006Willis, MTaylor, DGillmore, AEnolates derived from α-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd 2(dba) 3 and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C-S bond formation using identical reaction conditions and are converted to benzothiophene products. A cascade sequence that produces the required α-aryl ketones in situ has also been developed, although the substrate scope is more restricted. © 2006 Elsevier Ltd. All rights reserved. |
| spellingShingle | Willis, M Taylor, D Gillmore, A Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes |
| title | Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes |
| title_full | Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes |
| title_fullStr | Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes |
| title_full_unstemmed | Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes |
| title_short | Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes |
| title_sort | palladium catalysed intramolecular enolate o arylation and thio enolate s arylation synthesis of benzo b furans and benzo b thiophenes |
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