Iterative arylation of amino acids and aliphatic amines via δ‐C(sp3)−H activation: experimental and computational exploration
Directed C-H functionalization has been realized as a complementary tool to the traditional approaches for a straightforward access of non-proteinogenic amino acids; albeit such a process is restricted mostly up to the γ-position. In the present work, we demonstrate the diversification [(hetero)aryl...
| Hauptverfasser: | , , , , , , , , , |
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| Format: | Journal article |
| Sprache: | English |
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Wiley
2019
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| _version_ | 1826269009092280320 |
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| author | Guin, S Dolui, P Zhang, X Paul, S Singh, V Pradhan, S Chandrashekar, H Anjana, S Paton, RS Maiti, D |
| author_facet | Guin, S Dolui, P Zhang, X Paul, S Singh, V Pradhan, S Chandrashekar, H Anjana, S Paton, RS Maiti, D |
| author_sort | Guin, S |
| collection | OXFORD |
| description | Directed C-H functionalization has been realized as a complementary tool to the traditional approaches for a straightforward access of non-proteinogenic amino acids; albeit such a process is restricted mostly up to the γ-position. In the present work, we demonstrate the diversification [(hetero)arylation] of amino acids and analogous aliphatic amines selectively at the remote δ-position by tuning the reactivity controlled by ligands. An organopalladium δ-C(sp3)-H activated intermediate has been isolated and crystallographically characterized. Mechanistic investigations carried out experimentally in conjunction with computational studies shed light on the difference in the mechanistic picture depending on the substrate structure. |
| first_indexed | 2024-03-06T21:18:19Z |
| format | Journal article |
| id | oxford-uuid:408f6039-ba05-4c6f-8314-fe3be346125f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:18:19Z |
| publishDate | 2019 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:408f6039-ba05-4c6f-8314-fe3be346125f2022-03-26T14:38:47ZIterative arylation of amino acids and aliphatic amines via δ‐C(sp3)−H activation: experimental and computational explorationJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:408f6039-ba05-4c6f-8314-fe3be346125fEnglishSymplectic Elements at OxfordWiley2019Guin, SDolui, PZhang, XPaul, SSingh, VPradhan, SChandrashekar, HAnjana, SPaton, RSMaiti, DDirected C-H functionalization has been realized as a complementary tool to the traditional approaches for a straightforward access of non-proteinogenic amino acids; albeit such a process is restricted mostly up to the γ-position. In the present work, we demonstrate the diversification [(hetero)arylation] of amino acids and analogous aliphatic amines selectively at the remote δ-position by tuning the reactivity controlled by ligands. An organopalladium δ-C(sp3)-H activated intermediate has been isolated and crystallographically characterized. Mechanistic investigations carried out experimentally in conjunction with computational studies shed light on the difference in the mechanistic picture depending on the substrate structure. |
| spellingShingle | Guin, S Dolui, P Zhang, X Paul, S Singh, V Pradhan, S Chandrashekar, H Anjana, S Paton, RS Maiti, D Iterative arylation of amino acids and aliphatic amines via δ‐C(sp3)−H activation: experimental and computational exploration |
| title | Iterative arylation of amino acids and aliphatic amines via δ‐C(sp3)−H activation: experimental and computational exploration |
| title_full | Iterative arylation of amino acids and aliphatic amines via δ‐C(sp3)−H activation: experimental and computational exploration |
| title_fullStr | Iterative arylation of amino acids and aliphatic amines via δ‐C(sp3)−H activation: experimental and computational exploration |
| title_full_unstemmed | Iterative arylation of amino acids and aliphatic amines via δ‐C(sp3)−H activation: experimental and computational exploration |
| title_short | Iterative arylation of amino acids and aliphatic amines via δ‐C(sp3)−H activation: experimental and computational exploration |
| title_sort | iterative arylation of amino acids and aliphatic amines via δ c sp3 h activation experimental and computational exploration |
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