Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2016
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| Online Access: | http://hdl.handle.net/1721.1/104057 https://orcid.org/0000-0002-8750-7968 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826215100599500800 |
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| author | Colombe, James Robert DeBergh, John Robbins Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Colombe, James Robert DeBergh, John Robbins Buchwald, Stephen Leffler |
| author_sort | Colombe, James Robert |
| collection | MIT |
| description | A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides. |
| first_indexed | 2024-09-23T16:16:34Z |
| format | Article |
| id | mit-1721.1/104057 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:16:34Z |
| publishDate | 2016 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1040572022-09-29T19:20:34Z Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate Colombe, James Robert DeBergh, John Robbins Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Colombe, James Robert DeBergh, John Robbins Buchwald, Stephen Leffler A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides. National Institutes of Health (U.S.) (NIH grant (GM58160)) National Institutes of Health (U.S.) (NIH Supplement Award 3-R01-GM046059-20S) National Institutes of Health (U.S.) (NIH Fellowship (1F32GM099202)) National Science Foundation (U.S.) (NSF Graduate Research Fellowship, Grant 1122374) 2016-08-29T15:43:52Z 2016-08-29T15:43:52Z 2015-06 2015-05 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/104057 Colombe, James R., J. Robb DeBergh, and Stephen L. Buchwald. “Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.” Organic Letters 17, no. 12 (June 19, 2015): 3170–3173. © 2015 American Chemical Society. https://orcid.org/0000-0002-8750-7968 https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/acs.orglett.5b01540 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 | Colombe, James Robert DeBergh, John Robbins Buchwald, Stephen Leffler Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate |
| title | Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate |
| title_full | Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate |
| title_fullStr | Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate |
| title_full_unstemmed | Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate |
| title_short | Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate |
| title_sort | synthesis of heteroaryl sulfonamides from organozinc reagents and 2 4 6 trichlorophenyl chlorosulfate |
| url | http://hdl.handle.net/1721.1/104057 https://orcid.org/0000-0002-8750-7968 https://orcid.org/0000-0003-3875-4775 |
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