A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes
A series of air-stable nickel complexes of the form L[subscript 2]Ni(aryl) X (L = monodentate phosphine, X = Cl, Br) and LNi(aryl)X (L = bis-phosphine) have been synthesized and are presented as a library of precatalysts suitable for a wide variety of nickel-catalyzed transformations. These complexe...
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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/1721.1/97490 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826206058609115136 |
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| author | Smith, Stacey J. Jamison, Timothy F. Standley, Eric Mueller, Peter |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Smith, Stacey J. Jamison, Timothy F. Standley, Eric Mueller, Peter |
| author_sort | Smith, Stacey J. |
| collection | MIT |
| description | A series of air-stable nickel complexes of the form L[subscript 2]Ni(aryl) X (L = monodentate phosphine, X = Cl, Br) and LNi(aryl)X (L = bis-phosphine) have been synthesized and are presented as a library of precatalysts suitable for a wide variety of nickel-catalyzed transformations. These complexes are easily synthesized from low-cost NiCl[subscript 2]·6H[subscript 2]O or NiBr[subscript 2]·3H[subscript 2]O and the desired ligand followed by addition of 1 equiv of Grignard reagent. A selection of these complexes were characterized by single-crystal X-ray diffraction, and an analysis of their structural features is provided. A case study of their use as precatalysts for the nickel-catalyzed carbonyl-ene reaction is presented, showing superior reactivity in comparison to reactions using Ni(cod)[subscript 2]. Furthermore, as the precatalysts are all stable to air, no glovebox or inert-atmosphere techniques are required to make use of these complexes for nickel-catalyzed reactions. |
| first_indexed | 2024-09-23T13:23:26Z |
| format | Article |
| id | mit-1721.1/97490 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:23:26Z |
| publishDate | 2015 |
| publisher | American Chemical Society (ACS) |
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| spelling | mit-1721.1/974902022-09-28T13:50:44Z A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes Smith, Stacey J. Jamison, Timothy F. Standley, Eric Mueller, Peter Massachusetts Institute of Technology. Department of Chemistry Standley, Eric Smith, Stacey J. Mueller, Peter Jamison, Timothy F. A series of air-stable nickel complexes of the form L[subscript 2]Ni(aryl) X (L = monodentate phosphine, X = Cl, Br) and LNi(aryl)X (L = bis-phosphine) have been synthesized and are presented as a library of precatalysts suitable for a wide variety of nickel-catalyzed transformations. These complexes are easily synthesized from low-cost NiCl[subscript 2]·6H[subscript 2]O or NiBr[subscript 2]·3H[subscript 2]O and the desired ligand followed by addition of 1 equiv of Grignard reagent. A selection of these complexes were characterized by single-crystal X-ray diffraction, and an analysis of their structural features is provided. A case study of their use as precatalysts for the nickel-catalyzed carbonyl-ene reaction is presented, showing superior reactivity in comparison to reactions using Ni(cod)[subscript 2]. Furthermore, as the precatalysts are all stable to air, no glovebox or inert-atmosphere techniques are required to make use of these complexes for nickel-catalyzed reactions. National Institute of General Medical Sciences (U.S.) (GM63755) National Science Foundation (U.S.). Graduate Research Fellowship 2015-06-22T13:57:09Z 2015-06-22T13:57:09Z 2014-04 2014-02 Article http://purl.org/eprint/type/JournalArticle 0276-7333 1520-6041 http://hdl.handle.net/1721.1/97490 Standley, Eric A., Stacey J. Smith, Peter Müller, and Timothy F. Jamison. “A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes.” Organometallics 33, no. 8 (April 28, 2014): 2012–2018. © 2014 American Chemical Society https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1021/om500156q Organometallics 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) American Chemical Society |
| spellingShingle | Smith, Stacey J. Jamison, Timothy F. Standley, Eric Mueller, Peter A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes |
| title | A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes |
| title_full | A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes |
| title_fullStr | A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes |
| title_full_unstemmed | A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes |
| title_short | A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes |
| title_sort | broadly applicable strategy for entry into homogeneous nickel 0 catalysts from air stable nickel ii complexes |
| url | http://hdl.handle.net/1721.1/97490 https://orcid.org/0000-0002-8601-7799 |
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