A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted t...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2016
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| Online Access: | http://hdl.handle.net/1721.1/105162 https://orcid.org/0000-0003-3928-2984 https://orcid.org/0000-0001-8075-1100 https://orcid.org/0000-0003-3875-4775 |
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| author | Sather, Aaron C. Lee, Hong Geun De La Rosa, Valentina Y. Yang, Yang Mueller, Peter Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Sather, Aaron C. Lee, Hong Geun De La Rosa, Valentina Y. Yang, Yang Mueller, Peter Buchwald, Stephen Leffler |
| author_sort | Sather, Aaron C. |
| collection | MIT |
| description | A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1. |
| first_indexed | 2024-09-23T16:35:52Z |
| format | Article |
| id | mit-1721.1/105162 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:35:52Z |
| publishDate | 2016 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1051622022-10-02T08:22:57Z A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides Sather, Aaron C. Lee, Hong Geun De La Rosa, Valentina Y. Yang, Yang Mueller, Peter Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Sather, Aaron C. Lee, Hong Geun De La Rosa, Valentina Y. Yang, Yang Mueller, Peter Buchwald, Stephen Leffler A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1. National Institutes of Health (U.S.) (R01GM46059) National Institutes of Health (U.S.) (Postdoctoral fellowship (1F32GM108092-01A1) Massachusetts Institute of Technology. Undergraduate Research Opportunities Program 2016-11-01T17:01:32Z 2016-11-01T17:01:32Z 2015-09 2015-09 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/105162 Sather, Aaron C., Hong Geun Lee, Valentina Y. De La Rosa, Yang Yang, Peter Müller, and Stephen L. Buchwald. “A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides.” Journal of the American Chemical Society 137, no. 41 (October 21, 2015): 13433–13438. © 2015 American Chemical Society. https://orcid.org/0000-0003-3928-2984 https://orcid.org/0000-0001-8075-1100 https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/jacs.5b09308 Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) ACS |
| spellingShingle | Sather, Aaron C. Lee, Hong Geun De La Rosa, Valentina Y. Yang, Yang Mueller, Peter Buchwald, Stephen Leffler A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides |
| title | A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides |
| title_full | A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides |
| title_fullStr | A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides |
| title_full_unstemmed | A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides |
| title_short | A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides |
| title_sort | fluorinated ligand enables room temperature and regioselective pd catalyzed fluorination of aryl triflates and bromides |
| url | http://hdl.handle.net/1721.1/105162 https://orcid.org/0000-0003-3928-2984 https://orcid.org/0000-0001-8075-1100 https://orcid.org/0000-0003-3875-4775 |
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