Platinum-Catalyzed C–H Arylation of Simple Arenes
This report describes the Na2PtCl4 catalyzed C–H arylation of arene substrates with diaryliodonium salts. The site selectivity of these reactions is predominantly controlled by steric factors. Remarkably, Na2PtCl4-catalyzed naphthalene arylation proceeds with opposite site selectivity compared to th...
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| Veröffentlicht in: | Journal of the American Chemical Society 2013-10, Vol.135 (42), p.15710-15713 |
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| container_issue | 42 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 135 |
| creator | Wagner, Anna M Hickman, Amanda J Sanford, Melanie S |
| description | This report describes the Na2PtCl4 catalyzed C–H arylation of arene substrates with diaryliodonium salts. The site selectivity of these reactions is predominantly controlled by steric factors. Remarkably, Na2PtCl4-catalyzed naphthalene arylation proceeds with opposite site selectivity compared to that obtained with Na2PdCl4 as the catalyst. Preliminary mechanistic studies provide evidence for a PtII/PtIV catalytic cycle involving rate-limiting C–C bond-forming reductive elimination. |
| doi_str_mv | 10.1021/ja408112j |
| format | Article |
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The site selectivity of these reactions is predominantly controlled by steric factors. Remarkably, Na2PtCl4-catalyzed naphthalene arylation proceeds with opposite site selectivity compared to that obtained with Na2PdCl4 as the catalyst. Preliminary mechanistic studies provide evidence for a PtII/PtIV catalytic cycle involving rate-limiting C–C bond-forming reductive elimination.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja408112j</identifier><identifier>PMID: 24125480</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2013-10, Vol.135 (42), p.15710-15713</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-8e2104219a20c20aaaa67cd86b04999fe9e33b3fc35d561c427cab1d3d5271db3</citedby><cites>FETCH-LOGICAL-a315t-8e2104219a20c20aaaa67cd86b04999fe9e33b3fc35d561c427cab1d3d5271db3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja408112j$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja408112j$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24125480$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wagner, Anna M</creatorcontrib><creatorcontrib>Hickman, Amanda J</creatorcontrib><creatorcontrib>Sanford, Melanie S</creatorcontrib><title>Platinum-Catalyzed C–H Arylation of Simple Arenes</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>This report describes the Na2PtCl4 catalyzed C–H arylation of arene substrates with diaryliodonium salts. The site selectivity of these reactions is predominantly controlled by steric factors. Remarkably, Na2PtCl4-catalyzed naphthalene arylation proceeds with opposite site selectivity compared to that obtained with Na2PdCl4 as the catalyst. 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| source | ACS Publications |
| title | Platinum-Catalyzed C–H Arylation of Simple Arenes |
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