Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling.
A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the produc...
| Main Authors: | , , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2012
|
| _version_ | 1797100029323771904 |
|---|---|
| author | Hooper, J Chaplin, AB González-Rodríguez, C Thompson, A Weller, A Willis, M |
| author_facet | Hooper, J Chaplin, AB González-Rodríguez, C Thompson, A Weller, A Willis, M |
| author_sort | Hooper, J |
| collection | OXFORD |
| description | A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the products as an alkenyl sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process. |
| first_indexed | 2024-03-07T05:31:57Z |
| format | Journal article |
| id | oxford-uuid:e2921b8a-8740-4f2a-abfa-38b1805230a3 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:31:57Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:e2921b8a-8740-4f2a-abfa-38b1805230a32022-03-27T10:02:22ZAryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:e2921b8a-8740-4f2a-abfa-38b1805230a3EnglishSymplectic Elements at Oxford2012Hooper, JChaplin, ABGonzález-Rodríguez, CThompson, AWeller, AWillis, MA Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the products as an alkenyl sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process. |
| spellingShingle | Hooper, J Chaplin, AB González-Rodríguez, C Thompson, A Weller, A Willis, M Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. |
| title | Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. |
| title_full | Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. |
| title_fullStr | Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. |
| title_full_unstemmed | Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. |
| title_short | Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling. |
| title_sort | aryl methyl sulfides as substrates for rhodium catalyzed alkyne carbothiolation arene functionalization with activating group recycling |
| work_keys_str_mv | AT hooperj arylmethylsulfidesassubstratesforrhodiumcatalyzedalkynecarbothiolationarenefunctionalizationwithactivatinggrouprecycling AT chaplinab arylmethylsulfidesassubstratesforrhodiumcatalyzedalkynecarbothiolationarenefunctionalizationwithactivatinggrouprecycling AT gonzalezrodriguezc arylmethylsulfidesassubstratesforrhodiumcatalyzedalkynecarbothiolationarenefunctionalizationwithactivatinggrouprecycling AT thompsona arylmethylsulfidesassubstratesforrhodiumcatalyzedalkynecarbothiolationarenefunctionalizationwithactivatinggrouprecycling AT wellera arylmethylsulfidesassubstratesforrhodiumcatalyzedalkynecarbothiolationarenefunctionalizationwithactivatinggrouprecycling AT willism arylmethylsulfidesassubstratesforrhodiumcatalyzedalkynecarbothiolationarenefunctionalizationwithactivatinggrouprecycling |