Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization.
A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolat...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2013
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| _version_ | 1797058534708346880 |
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| author | Pilgrim, B Gatland, A McTernan, C Procopiou, P Donohoe, T |
| author_facet | Pilgrim, B Gatland, A McTernan, C Procopiou, P Donohoe, T |
| author_sort | Pilgrim, B |
| collection | OXFORD |
| description | A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield. |
| first_indexed | 2024-03-06T19:51:39Z |
| format | Journal article |
| id | oxford-uuid:242a7378-7188-496e-bb32-5588f14207d8 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:51:39Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | oxford-uuid:242a7378-7188-496e-bb32-5588f14207d82022-03-26T11:48:28ZModular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:242a7378-7188-496e-bb32-5588f14207d8EnglishSymplectic Elements at Oxford2013Pilgrim, BGatland, AMcTernan, CProcopiou, PDonohoe, TA methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladium catalyzed α-arylation reaction of an enolate, followed by in situ trapping with an electrophile, and aromatization with ammonium chloride. tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield. |
| spellingShingle | Pilgrim, B Gatland, A McTernan, C Procopiou, P Donohoe, T Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization. |
| title | Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization. |
| title_full | Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization. |
| title_fullStr | Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization. |
| title_full_unstemmed | Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization. |
| title_short | Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization. |
| title_sort | modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization |
| work_keys_str_mv | AT pilgrimb modularisoquinolinesynthesisusingcatalyticenolatearylationandinsitufunctionalization AT gatlanda modularisoquinolinesynthesisusingcatalyticenolatearylationandinsitufunctionalization AT mcternanc modularisoquinolinesynthesisusingcatalyticenolatearylationandinsitufunctionalization AT procopioup modularisoquinolinesynthesisusingcatalyticenolatearylationandinsitufunctionalization AT donohoet modularisoquinolinesynthesisusingcatalyticenolatearylationandinsitufunctionalization |