N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings
A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free −NH[subscript 2] group from contaminating cross-coupling products. These...
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| Format: | Article |
| Language: | en_US |
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2015
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| Online Access: | http://hdl.handle.net/1721.1/97471 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826206540785254400 |
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| author | Bruno, Nicholas C. Niljianskul, Nootaree Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Bruno, Nicholas C. Niljianskul, Nootaree Buchwald, Stephen Leffler |
| author_sort | Bruno, Nicholas C. |
| collection | MIT |
| description | A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free −NH[subscript 2] group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki–Miyaura and C–N cross-coupling reactions. |
| first_indexed | 2024-09-23T13:34:33Z |
| format | Article |
| id | mit-1721.1/97471 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:34:33Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | mit-1721.1/974712022-10-01T15:45:21Z N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings Bruno, Nicholas C. Niljianskul, Nootaree Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Bruno, Nicholas C. Niljianskul, Nootaree Buchwald, Stephen Leffler A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free −NH[subscript 2] group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki–Miyaura and C–N cross-coupling reactions. National Institutes of Health (U.S.) (GM46059) National Institutes of Health (U.S.) (GM58160) 2015-06-19T14:57:15Z 2015-06-19T14:57:15Z 2014-04 2014-02 Article http://purl.org/eprint/type/JournalArticle 0022-3263 1520-6904 http://hdl.handle.net/1721.1/97471 Bruno, Nicholas C., Nootaree Niljianskul, and Stephen L. Buchwald. “N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings.” The Journal of Organic Chemistry 79, no. 9 (May 2, 2014): 4161–4166. © 2014 American Chemical Society https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/jo500355k The Journal of Organic Chemistry 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 |
| spellingShingle | Bruno, Nicholas C. Niljianskul, Nootaree Buchwald, Stephen Leffler N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings |
| title | N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings |
| title_full | N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings |
| title_fullStr | N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings |
| title_full_unstemmed | N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings |
| title_short | N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings |
| title_sort | n substituted 2 aminobiphenylpalladium methanesulfonate precatalysts and their use in c c and c n cross couplings |
| url | http://hdl.handle.net/1721.1/97471 https://orcid.org/0000-0003-3875-4775 |
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