An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors
An investigation into Pd-catalyzed C−N cross-coupling reactions of aryl iodides is described. NaI is shown to have a significant inhibitory effect on these processes. By switching to a solvent system in which the iodide byproduct was insoluble, reactions of aryl iodides were accomplished with the sa...
| Main Authors: | , , |
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2013
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| Online Access: | http://hdl.handle.net/1721.1/82102 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1811084412158214144 |
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| author | Fors, Brett P. Buchwald, Stephen Leffler Davis, Nicole Rose |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Fors, Brett P. Buchwald, Stephen Leffler Davis, Nicole Rose |
| author_sort | Fors, Brett P. |
| collection | MIT |
| description | An investigation into Pd-catalyzed C−N cross-coupling reactions of aryl iodides is described. NaI is shown to have a significant inhibitory effect on these processes. By switching to a solvent system in which the iodide byproduct was insoluble, reactions of aryl iodides were accomplished with the same efficiencies as aryl chlorides and bromides. Using catalyst systems based on certain biarylphosphine ligands, aryl iodides were successfully reacted with an array of primary and secondary amines in high yields. Lastly, reactions of heteroarylamines and heteroaryliodides were also conducted in high yields. |
| first_indexed | 2024-09-23T12:50:18Z |
| format | Article |
| id | mit-1721.1/82102 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T12:50:18Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/821022022-10-01T11:25:06Z An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors Fors, Brett P. Buchwald, Stephen Leffler Davis, Nicole Rose Massachusetts Institute of Technology. Department of Chemistry Buchwald, Stephen Leffler Fors, Brett P. Davis, Nicole Rose An investigation into Pd-catalyzed C−N cross-coupling reactions of aryl iodides is described. NaI is shown to have a significant inhibitory effect on these processes. By switching to a solvent system in which the iodide byproduct was insoluble, reactions of aryl iodides were accomplished with the same efficiencies as aryl chlorides and bromides. Using catalyst systems based on certain biarylphosphine ligands, aryl iodides were successfully reacted with an array of primary and secondary amines in high yields. Lastly, reactions of heteroarylamines and heteroaryliodides were also conducted in high yields. National Institutes of Health (U.S.) (Grant GM-58160) Merck & Co., Inc. BASF Chemetall William Asbornsen Albert Memorial Fund (Fellowship) National Science Foundation (U.S.) (Grant CHE 9808061) National Science Foundation (U.S.) (Grant DBI 9729592) 2013-11-13T15:56:34Z 2013-11-13T15:56:34Z 2009-04 2009-02 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/82102 Fors, Brett P., Nicole R. Davis, and Stephen L. Buchwald. “An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors.” Journal of the American Chemical Society 131, no. 16 (April 29, 2009): 5766-5768. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/ja901414u 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) PMC |
| spellingShingle | Fors, Brett P. Buchwald, Stephen Leffler Davis, Nicole Rose An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors |
| title | An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors |
| title_full | An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors |
| title_fullStr | An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors |
| title_full_unstemmed | An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors |
| title_short | An Efficient Process for Pd-Catalyzed C−N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors |
| title_sort | efficient process for pd catalyzed c n cross coupling reactions of aryl iodides insight into controlling factors |
| url | http://hdl.handle.net/1721.1/82102 https://orcid.org/0000-0003-3875-4775 |
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