Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols
Construction of C–C bonds utilizing challenging alkenyl alcohols employing first-row transition-metal catalysts is an unexplored area. Herein, we report the α-alkylation of ketones and nitriles using unactivated alkenyl alcohols as coupling partners in the presence of a phosphine-free pincer-NHC car...
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2024
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| _version_ | 1852024137594175488 |
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| author | Adarsha Mandal (13876919) |
| author2 | Manoj Pradhan (12067271) Chirantan Mitra (20473299) Srabani Nandi (15451796) Biswajit Sadhu (1431220) Sabuj Kundu (1787752) |
| author2_role | author author author author author |
| author_facet | Adarsha Mandal (13876919) Manoj Pradhan (12067271) Chirantan Mitra (20473299) Srabani Nandi (15451796) Biswajit Sadhu (1431220) Sabuj Kundu (1787752) |
| author_role | author |
| dc.creator.none.fl_str_mv | Adarsha Mandal (13876919) Manoj Pradhan (12067271) Chirantan Mitra (20473299) Srabani Nandi (15451796) Biswajit Sadhu (1431220) Sabuj Kundu (1787752) |
| dc.date.none.fl_str_mv | 2024-12-24T17:15:13Z |
| dc.identifier.none.fl_str_mv | 10.1021/acscatal.4c05889.s002 |
| dc.relation.none.fl_str_mv | https://figshare.com/articles/dataset/Pincer-_NHC_Mn_I_Complex-Catalyzed_Selective_Alkylation_of_Ketones_and_Nitriles_Using_Unactivated_Alkenyl_Alcohols/28090563 |
| dc.rights.none.fl_str_mv | CC BY-NC 4.0 info:eu-repo/semantics/openAccess |
| dc.subject.none.fl_str_mv | Biophysics Biochemistry Molecular Biology Biotechnology Sociology Infectious Diseases Chemical Sciences not elsewhere classified several control experiments green chemistry metrics density functional theory pincer -( nhc nhc carbene free pincer wide variety unexplored area synthetic value scale synthesis row transition reaction mechanism practical applicability metal catalysts kinetic studies important molecules highly effective hammett studies coupling partners catalytic system alkylated products aliphatic units |
| dc.title.none.fl_str_mv | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols |
| dc.type.none.fl_str_mv | Dataset info:eu-repo/semantics/publishedVersion dataset |
| description | Construction of C–C bonds utilizing challenging alkenyl alcohols employing first-row transition-metal catalysts is an unexplored area. Herein, we report the α-alkylation of ketones and nitriles using unactivated alkenyl alcohols as coupling partners in the presence of a phosphine-free pincer-NHC carbene-Mn(I) complex. This catalytic system was highly effective for the α-alkylation of a wide variety of ketones and acetonitriles having aromatic, heteroaromatic, and aliphatic units in the presence of several reducible functional groups. The practical applicability and synthetic value of this protocol were demonstrated through gram-scale synthesis, evaluation of green chemistry metrics, and functionalization of alkylated products into important molecules. Several control experiments, kinetic studies, and Hammett studies were carried out to understand the reaction mechanism, which was further supported by density functional theory (DFT) calculations. |
| eu_rights_str_mv | openAccess |
| id | Manara_ebeaf2e7f2bd01e033fe416cc81556e8 |
| identifier_str_mv | 10.1021/acscatal.4c05889.s002 |
| network_acronym_str | Manara |
| network_name_str | ManaraRepo |
| oai_identifier_str | oai:figshare.com:article/28090563 |
| publishDate | 2024 |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| rights_invalid_str_mv | CC BY-NC 4.0 |
| spelling | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl AlcoholsAdarsha Mandal (13876919)Manoj Pradhan (12067271)Chirantan Mitra (20473299)Srabani Nandi (15451796)Biswajit Sadhu (1431220)Sabuj Kundu (1787752)BiophysicsBiochemistryMolecular BiologyBiotechnologySociologyInfectious DiseasesChemical Sciences not elsewhere classifiedseveral control experimentsgreen chemistry metricsdensity functional theorypincer -( nhcnhc carbenefree pincerwide varietyunexplored areasynthetic valuescale synthesisrow transitionreaction mechanismpractical applicabilitymetal catalystskinetic studiesimportant moleculeshighly effectivehammett studiescoupling partnerscatalytic systemalkylated productsaliphatic unitsConstruction of C–C bonds utilizing challenging alkenyl alcohols employing first-row transition-metal catalysts is an unexplored area. Herein, we report the α-alkylation of ketones and nitriles using unactivated alkenyl alcohols as coupling partners in the presence of a phosphine-free pincer-NHC carbene-Mn(I) complex. This catalytic system was highly effective for the α-alkylation of a wide variety of ketones and acetonitriles having aromatic, heteroaromatic, and aliphatic units in the presence of several reducible functional groups. The practical applicability and synthetic value of this protocol were demonstrated through gram-scale synthesis, evaluation of green chemistry metrics, and functionalization of alkylated products into important molecules. Several control experiments, kinetic studies, and Hammett studies were carried out to understand the reaction mechanism, which was further supported by density functional theory (DFT) calculations.2024-12-24T17:15:13ZDatasetinfo:eu-repo/semantics/publishedVersiondataset10.1021/acscatal.4c05889.s002https://figshare.com/articles/dataset/Pincer-_NHC_Mn_I_Complex-Catalyzed_Selective_Alkylation_of_Ketones_and_Nitriles_Using_Unactivated_Alkenyl_Alcohols/28090563CC BY-NC 4.0info:eu-repo/semantics/openAccessoai:figshare.com:article/280905632024-12-24T17:15:13Z |
| spellingShingle | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols Adarsha Mandal (13876919) Biophysics Biochemistry Molecular Biology Biotechnology Sociology Infectious Diseases Chemical Sciences not elsewhere classified several control experiments green chemistry metrics density functional theory pincer -( nhc nhc carbene free pincer wide variety unexplored area synthetic value scale synthesis row transition reaction mechanism practical applicability metal catalysts kinetic studies important molecules highly effective hammett studies coupling partners catalytic system alkylated products aliphatic units |
| status_str | publishedVersion |
| title | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols |
| title_full | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols |
| title_fullStr | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols |
| title_full_unstemmed | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols |
| title_short | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols |
| title_sort | Pincer-(NHC)Mn(I) Complex-Catalyzed Selective α‑Alkylation of Ketones and Nitriles Using Unactivated Alkenyl Alcohols |
| topic | Biophysics Biochemistry Molecular Biology Biotechnology Sociology Infectious Diseases Chemical Sciences not elsewhere classified several control experiments green chemistry metrics density functional theory pincer -( nhc nhc carbene free pincer wide variety unexplored area synthetic value scale synthesis row transition reaction mechanism practical applicability metal catalysts kinetic studies important molecules highly effective hammett studies coupling partners catalytic system alkylated products aliphatic units |