Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes
A Ni-catalyzed reductive coupling of alkynes and epoxides using Ni(II) salts and simple alcohol reducing agents is described. Whereas previously reported conditions relied on Ni(cod)2 and Et3B, this system has several advantages including the use of air-stable and inexpensive Ni(II) precatalysts (e....
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| Format: | Article |
| Language: | en_US |
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American Chemical Society
2013
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| Online Access: | http://hdl.handle.net/1721.1/76709 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826215572372717568 |
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| author | Beaver, Matthew G. Jamison, Timothy F. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Beaver, Matthew G. Jamison, Timothy F. |
| author_sort | Beaver, Matthew G. |
| collection | MIT |
| description | A Ni-catalyzed reductive coupling of alkynes and epoxides using Ni(II) salts and simple alcohol reducing agents is described. Whereas previously reported conditions relied on Ni(cod)2 and Et3B, this system has several advantages including the use of air-stable and inexpensive Ni(II) precatalysts (e.g., NiBr2·3H2O) as the source of Ni(0) and simple alcohols (e.g., 2-propanol) as the reducing agent. Deuterium-labeling experiments are consistent with oxidative addition of an epoxide C–O bond that occurs with inversion of configuration. |
| first_indexed | 2024-09-23T16:35:44Z |
| format | Article |
| id | mit-1721.1/76709 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:35:44Z |
| publishDate | 2013 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | mit-1721.1/767092022-10-02T08:19:54Z Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes Beaver, Matthew G. Jamison, Timothy F. Massachusetts Institute of Technology. Department of Chemistry Jamison, Timothy F. Beaver, Matthew G. Jamison, Timothy F. A Ni-catalyzed reductive coupling of alkynes and epoxides using Ni(II) salts and simple alcohol reducing agents is described. Whereas previously reported conditions relied on Ni(cod)2 and Et3B, this system has several advantages including the use of air-stable and inexpensive Ni(II) precatalysts (e.g., NiBr2·3H2O) as the source of Ni(0) and simple alcohols (e.g., 2-propanol) as the reducing agent. Deuterium-labeling experiments are consistent with oxidative addition of an epoxide C–O bond that occurs with inversion of configuration. National Institutes of Health (U.S.) National Institute of General Medical Sciences (U.S.) (GM72566) National Institute of General Medical Sciences (U.S.) (GM63755) National Institutes of Health (U.S.) (postdoctoral fellowship (F32GM095014)) 2013-01-31T21:17:37Z 2013-01-31T21:17:37Z 2011-06 2011-06 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/76709 Beaver, Matthew G., and Timothy F. Jamison. “Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes.” Organic Letters 13.15 (2011): 4140–4143. Web. https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1021/ol201702a 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 Prof. Jamison via Erja Kajosalo |
| spellingShingle | Beaver, Matthew G. Jamison, Timothy F. Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes |
| title | Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes |
| title_full | Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes |
| title_fullStr | Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes |
| title_full_unstemmed | Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes |
| title_short | Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes |
| title_sort | ni ii salts and 2 propanol effect catalytic reductive coupling of epoxides and alkynes |
| url | http://hdl.handle.net/1721.1/76709 https://orcid.org/0000-0002-8601-7799 |
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