Fully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halides
Herein, we present a novel C(sp3)–C(sp3) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this reaction could be used for both library synthe...
| Main Authors: | , , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
American Chemical Society
2023
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| _version_ | 1797111354347225088 |
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| author | Pijper, B Martín, R Huertas-Alonso, AJ Linares, ML López, E Llaveria, J Díaz-Ortiz, Á Dixon, DJ de la Hoz, A Alcázar, J |
| author_facet | Pijper, B Martín, R Huertas-Alonso, AJ Linares, ML López, E Llaveria, J Díaz-Ortiz, Á Dixon, DJ de la Hoz, A Alcázar, J |
| author_sort | Pijper, B |
| collection | OXFORD |
| description | Herein, we present a novel C(sp3)–C(sp3) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this reaction could be used for both library synthesis and target molecule synthesis on the gram-scale starting from bench-stable reagents. Additionally, excellent chemoselectivity and functional group tolerance make it ideal for late-stage diversification of druglike molecules. |
| first_indexed | 2024-03-07T08:09:11Z |
| format | Journal article |
| id | oxford-uuid:2a296db3-e870-45b8-8052-4a3597e15dba |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T08:09:11Z |
| publishDate | 2023 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:2a296db3-e870-45b8-8052-4a3597e15dba2023-11-15T14:23:32ZFully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halidesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2a296db3-e870-45b8-8052-4a3597e15dbaEnglishSymplectic ElementsAmerican Chemical Society2023Pijper, BMartín, RHuertas-Alonso, AJLinares, MLLópez, ELlaveria, JDíaz-Ortiz, ÁDixon, DJde la Hoz, AAlcázar, JHerein, we present a novel C(sp3)–C(sp3) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this reaction could be used for both library synthesis and target molecule synthesis on the gram-scale starting from bench-stable reagents. Additionally, excellent chemoselectivity and functional group tolerance make it ideal for late-stage diversification of druglike molecules. |
| spellingShingle | Pijper, B Martín, R Huertas-Alonso, AJ Linares, ML López, E Llaveria, J Díaz-Ortiz, Á Dixon, DJ de la Hoz, A Alcázar, J Fully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halides |
| title | Fully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halides |
| title_full | Fully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halides |
| title_fullStr | Fully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halides |
| title_full_unstemmed | Fully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halides |
| title_short | Fully automated flow protocol for C(sp3)–C(sp3) bond formation from tertiary amides and alkyl halides |
| title_sort | fully automated flow protocol for c sp3 c sp3 bond formation from tertiary amides and alkyl halides |
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