Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization
A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C–H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction prot...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
| Published: |
American Chemical Society (ACS)
2013
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| Online Access: | http://hdl.handle.net/1721.1/81976 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826210571130765312 |
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| author | Cheung, Chi Wai Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Cheung, Chi Wai Buchwald, Stephen Leffler |
| author_sort | Cheung, Chi Wai |
| collection | MIT |
| description | A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C–H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles. |
| first_indexed | 2024-09-23T14:52:04Z |
| format | Article |
| id | mit-1721.1/81976 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T14:52:04Z |
| publishDate | 2013 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/819762022-09-29T11:03:20Z Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization Cheung, Chi Wai Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Cheung, Chi Wai Buchwald, Stephen Leffler A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C–H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles. National Institutes of Health (U.S.) (Grant GM58160) 2013-11-04T17:19:54Z 2013-11-04T17:19:54Z 2012-07 2012-06 Article http://purl.org/eprint/type/JournalArticle 0022-3263 1520-6904 http://hdl.handle.net/1721.1/81976 Cheung, Chi Wai, and Stephen L. Buchwald. “Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization.” The Journal of Organic Chemistry 77, no. 17 (September 7, 2012): 7526-7537. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/jo301332s 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 (ACS) PMC |
| spellingShingle | Cheung, Chi Wai Buchwald, Stephen Leffler Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization |
| title | Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization |
| title_full | Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization |
| title_fullStr | Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization |
| title_full_unstemmed | Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization |
| title_short | Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization |
| title_sort | room temperature copper ii catalyzed oxidative cyclization of enamides to 2 5 disubstituted oxazoles via vinylic c h functionalization |
| url | http://hdl.handle.net/1721.1/81976 https://orcid.org/0000-0003-3875-4775 |
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