Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine
Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed as the supporting ligand. In each of t...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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Elsevier
2015
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| Online Access: | http://hdl.handle.net/1721.1/99485 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826198956036587520 |
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| author | Lee, Brian K. Biscoe, Mark R. Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Lee, Brian K. Biscoe, Mark R. Buchwald, Stephen Leffler |
| author_sort | Lee, Brian K. |
| collection | MIT |
| description | Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed as the supporting ligand. In each of these cases, commercially available solutions constitute the source of the dimethylamine, and recently disclosed precatalysts constitute the source of the ligand and Pd. This work further expands the utility of these precatalysts in reactions that benefit from an easily activated source of L[subscript 1]Pd(0). |
| first_indexed | 2024-09-23T11:12:29Z |
| format | Article |
| id | mit-1721.1/99485 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T11:12:29Z |
| publishDate | 2015 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | mit-1721.1/994852022-10-01T02:01:36Z Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine Lee, Brian K. Biscoe, Mark R. Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Lee, Brian K. Biscoe, Mark R. Buchwald, Stephen Leffler Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed as the supporting ligand. In each of these cases, commercially available solutions constitute the source of the dimethylamine, and recently disclosed precatalysts constitute the source of the ligand and Pd. This work further expands the utility of these precatalysts in reactions that benefit from an easily activated source of L[subscript 1]Pd(0). National Institutes of Health (U.S.) (GM-058160) National Institutes of Health (U.S.) (Postdoctoral Fellowship GM-F32-75685) Amgen Inc. Merck & Co., Inc. Boehringer Ingelheim Pharmaceuticals Massachusetts Institute of Technology. Undergraduate Research Opportunities Program (Summer Fellowship) 2015-10-28T13:00:35Z 2015-10-28T13:00:35Z 2009-03 2009-03 Article http://purl.org/eprint/type/JournalArticle 00404039 http://hdl.handle.net/1721.1/99485 Lee, Brian K., Mark R. Biscoe, and Stephen L. Buchwald. “Simple, Efficient Protocols for the Pd-Catalyzed Cross-Coupling Reaction of Aryl Chlorides and Dimethylamine.” Tetrahedron Letters 50, no. 26 (July 2009): 3672–3674. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1016/j.tetlet.2009.03.137 Tetrahedron Letters Creative Commons Attribution-Noncommercial-NoDerivatives http://creativecommons.org/licenses/by-nc-nd/4.0/ application/pdf Elsevier PMC |
| spellingShingle | Lee, Brian K. Biscoe, Mark R. Buchwald, Stephen Leffler Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine |
| title | Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine |
| title_full | Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine |
| title_fullStr | Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine |
| title_full_unstemmed | Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine |
| title_short | Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine |
| title_sort | simple efficient protocols for the pd catalyzed cross coupling reaction of aryl chlorides and dimethylamine |
| url | http://hdl.handle.net/1721.1/99485 https://orcid.org/0000-0003-3875-4775 |
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