Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides
The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates....
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2015
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| Online Access: | http://hdl.handle.net/1721.1/99659 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826206256838213632 |
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| author | Yang, Yang Niedermann, Katrin Han, Chong Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Yang, Yang Niedermann, Katrin Han, Chong Buchwald, Stephen Leffler |
| author_sort | Yang, Yang |
| collection | MIT |
| description | The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes. |
| first_indexed | 2024-09-23T13:26:34Z |
| format | Article |
| id | mit-1721.1/99659 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:26:34Z |
| publishDate | 2015 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/996592022-10-01T15:17:58Z Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides Yang, Yang Niedermann, Katrin Han, Chong Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Yang, Yang Niedermann, Katrin Han, Chong Buchwald, Stephen Leffler The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes. National Institutes of Health (U.S.) (Grant GM46059) Swiss National Science Foundation (Postdoctoral Fellowship) 2015-11-02T19:13:16Z 2015-11-02T19:13:16Z 2014-08 2014-07 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/99659 Yang, Yang, Katrin Niedermann, Chong Han, and Stephen L. Buchwald. “Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides.” Organic Letters 16, no. 17 (September 5, 2014): 4638–4641. © 2014 American Chemical Society https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/ol502230p 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) ACS |
| spellingShingle | Yang, Yang Niedermann, Katrin Han, Chong Buchwald, Stephen Leffler Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides |
| title | Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides |
| title_full | Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides |
| title_fullStr | Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides |
| title_full_unstemmed | Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides |
| title_short | Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides |
| title_sort | highly selective palladium catalyzed cross coupling of secondary alkylzinc reagents with heteroaryl halides |
| url | http://hdl.handle.net/1721.1/99659 https://orcid.org/0000-0003-3875-4775 |
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