Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands
In this report, we describe the application of palladium-based oxidative addition complexes (OACs) as effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts...
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| Format: | Article |
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American Chemical Society (ACS)
2018
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| Online Access: | http://hdl.handle.net/1721.1/116337 https://orcid.org/0000-0002-9049-6227 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826212369243570176 |
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| author | Ingoglia, Bryan Taylor Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Ingoglia, Bryan Taylor Buchwald, Stephen Leffler |
| author_sort | Ingoglia, Bryan Taylor |
| collection | MIT |
| description | In this report, we describe the application of palladium-based oxidative addition complexes (OACs) as effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts, particularly in the case of the bulkiest biarylphosphine ligands, for which palladacycle-based precatalysts do not readily form. The precatalysts described herein are easily prepared and stable to long-term storage under air. |
| first_indexed | 2024-09-23T15:20:37Z |
| format | Article |
| id | mit-1721.1/116337 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T15:20:37Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1163372022-09-29T14:21:49Z Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands Ingoglia, Bryan Taylor Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Ingoglia, Bryan Taylor Buchwald, Stephen Leffler In this report, we describe the application of palladium-based oxidative addition complexes (OACs) as effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts, particularly in the case of the bulkiest biarylphosphine ligands, for which palladacycle-based precatalysts do not readily form. The precatalysts described herein are easily prepared and stable to long-term storage under air. National Institutes of Health (U.S.) (Award GM46059) National Institutes of Health (U.S.) (Award GM58160) 2018-06-15T15:30:35Z 2018-06-15T15:30:35Z 2017-06 2017-04 2018-06-13T15:08:00Z Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/116337 Ingoglia, Bryan T. and Stephen L. Buchwald. “Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands.” Organic Letters 19, 11 (May 2017): 2853–2856 © 2017 American Chemical Society https://orcid.org/0000-0002-9049-6227 https://orcid.org/0000-0003-3875-4775 http://dx.doi.org/10.1021/ACS.ORGLETT.7B01082 Organic Letters 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 | Ingoglia, Bryan Taylor Buchwald, Stephen Leffler Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands |
| title | Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands |
| title_full | Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands |
| title_fullStr | Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands |
| title_full_unstemmed | Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands |
| title_short | Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands |
| title_sort | oxidative addition complexes as precatalysts for cross coupling reactions requiring extremely bulky biarylphosphine ligands |
| url | http://hdl.handle.net/1721.1/116337 https://orcid.org/0000-0002-9049-6227 https://orcid.org/0000-0003-3875-4775 |
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