| Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate. | |
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MedLine Citation:
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PMID: 22524190 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture-sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF(4)). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups. |
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Authors:
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Gary A Molander; Livia N Cavalcanti |
Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2012-04-24 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 77 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2012 May |
Date Detail:
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Created Date: 2012-05-04 Completed Date: 2012-09-28 Revised Date: 2013-05-06 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 4402-13 Citation Subset: IM |
Affiliation:
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Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Borates
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chemical synthesis,
chemistry* Catalysis Heterocyclic Compounds / chemistry* Molecular Structure Nitric Oxide / chemical synthesis*, chemistry* Nitrosation |
| Grant Support | |
ID/Acronym/Agency:
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GM035249/GM/NIGMS NIH HHS; R01 GM035249/GM/NIGMS NIH HHS; R01 GM081376/GM/NIGMS NIH HHS; R01 GM086209/GM/NIGMS NIH HHS; S10 RR016640/RR/NCRR NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Borates; 0/Heterocyclic Compounds; 10102-43-9/Nitric Oxide; 14635-75-7/nitrosonium tetrafluoroborate |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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