Ligand‐ and Solvent‐Tuned Chemoselective Carbonylation of Bromoaryl Triflates
The palladium‐catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C−Br bond versus C−OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene (Xantphos) vs. 1,1′‐bis(diphen...
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| Veröffentlicht in: | Chemistry : a European journal 2017-09, Vol.23 (54), p.13369-13378 |
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| container_title | Chemistry : a European journal |
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| creator | Shen, Chaoren Wei, Zhihong Jiao, Haijun Wu, Xiao‐Feng |
| description | The palladium‐catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C−Br bond versus C−OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene (Xantphos) vs. 1,1′‐bis(diphenylphosphino)ferrocene (DPPF)] and the solvent (toluene vs. DMSO). The respective ligand and solvent effects are rationalized by DFT calculations. In contrast, the monodentate ligands BuPAd2 and tBu3P prefer the selective C−Br bond activation and are solvent insensitive.
Keep control: Palladium‐catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The influencing effects of different solvents (polar vs. non‐polar) and ligands (e.g., monodentate vs. bidentate) on the chemoselectivety is discussed based on experimental observations as well as DFT calculations (see scheme; Xantphos=4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene, DPPF=1,1′‐bis(diphenylphosphino)ferrocene). |
| doi_str_mv | 10.1002/chem.201702015 |
| format | Article |
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Keep control: Palladium‐catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The influencing effects of different solvents (polar vs. non‐polar) and ligands (e.g., monodentate vs. bidentate) on the chemoselectivety is discussed based on experimental observations as well as DFT calculations (see scheme; Xantphos=4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene, DPPF=1,1′‐bis(diphenylphosphino)ferrocene).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201702015</identifier><identifier>PMID: 28650074</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>bromoaryl triflates ; carbonylation ; Carbonyls ; Chemistry ; chemoselectivity ; Ligands ; Palladium ; solvent effects ; Solvents ; Toluene</subject><ispartof>Chemistry : a European journal, 2017-09, Vol.23 (54), p.13369-13378</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4765-6aad01bb03fb871ab3cb9d87a90d1834e35ddf4030c3fd065f80d748e4f28fe3</citedby><cites>FETCH-LOGICAL-c4765-6aad01bb03fb871ab3cb9d87a90d1834e35ddf4030c3fd065f80d748e4f28fe3</cites><orcidid>0000-0001-6622-3328</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201702015$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201702015$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28650074$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shen, Chaoren</creatorcontrib><creatorcontrib>Wei, Zhihong</creatorcontrib><creatorcontrib>Jiao, Haijun</creatorcontrib><creatorcontrib>Wu, Xiao‐Feng</creatorcontrib><title>Ligand‐ and Solvent‐Tuned Chemoselective Carbonylation of Bromoaryl Triflates</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>The palladium‐catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C−Br bond versus C−OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene (Xantphos) vs. 1,1′‐bis(diphenylphosphino)ferrocene (DPPF)] and the solvent (toluene vs. DMSO). The respective ligand and solvent effects are rationalized by DFT calculations. In contrast, the monodentate ligands BuPAd2 and tBu3P prefer the selective C−Br bond activation and are solvent insensitive.
Keep control: Palladium‐catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The influencing effects of different solvents (polar vs. non‐polar) and ligands (e.g., monodentate vs. bidentate) on the chemoselectivety is discussed based on experimental observations as well as DFT calculations (see scheme; Xantphos=4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene, DPPF=1,1′‐bis(diphenylphosphino)ferrocene).</description><subject>bromoaryl triflates</subject><subject>carbonylation</subject><subject>Carbonyls</subject><subject>Chemistry</subject><subject>chemoselectivity</subject><subject>Ligands</subject><subject>Palladium</subject><subject>solvent effects</subject><subject>Solvents</subject><subject>Toluene</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LxDAQhoMoun5cPUrBi5eukyZt06MWv2BFxN5L2ky0S9usyXZlb_4Ef6O_xCy7KnjxkiHDMy8zDyHHFMYUIDqvX7AbR0BT8E-8RUY0jmjI0iTeJiPIeBomMcv2yL5zUwDIEsZ2yV4kkhgg5SPyOGmeZa8-3z8CX4In0y6wn_tvMfSogtzHG4ct1vNmgUEubWX6ZSvnjekDo4NLazoj7bINCtto30d3SHa0bB0ebeoBKa6vivw2nDzc3OUXk7DmfrswkVIBrSpguhIplRWrq0yJVGagqGAcWayU5sCgZlpBEmsBKuUCuY6ERnZAztaxM2teB3TzsmtcjW0rezSDK2lGmWCRELFHT_-gUzPY3i_nKc7Aq-CRp8ZrqrbGOYu6nNmm87eVFMqV63Lluvxx7QdONrFD1aH6wb_leiBbA29Ni8t_4sr89ur-N_wLXlmMwg</recordid><startdate>20170927</startdate><enddate>20170927</enddate><creator>Shen, Chaoren</creator><creator>Wei, Zhihong</creator><creator>Jiao, Haijun</creator><creator>Wu, Xiao‐Feng</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6622-3328</orcidid></search><sort><creationdate>20170927</creationdate><title>Ligand‐ and Solvent‐Tuned Chemoselective Carbonylation of Bromoaryl Triflates</title><author>Shen, Chaoren ; Wei, Zhihong ; Jiao, Haijun ; Wu, Xiao‐Feng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4765-6aad01bb03fb871ab3cb9d87a90d1834e35ddf4030c3fd065f80d748e4f28fe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>bromoaryl triflates</topic><topic>carbonylation</topic><topic>Carbonyls</topic><topic>Chemistry</topic><topic>chemoselectivity</topic><topic>Ligands</topic><topic>Palladium</topic><topic>solvent effects</topic><topic>Solvents</topic><topic>Toluene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shen, Chaoren</creatorcontrib><creatorcontrib>Wei, Zhihong</creatorcontrib><creatorcontrib>Jiao, Haijun</creatorcontrib><creatorcontrib>Wu, Xiao‐Feng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shen, Chaoren</au><au>Wei, Zhihong</au><au>Jiao, Haijun</au><au>Wu, Xiao‐Feng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ligand‐ and Solvent‐Tuned Chemoselective Carbonylation of Bromoaryl Triflates</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2017-09-27</date><risdate>2017</risdate><volume>23</volume><issue>54</issue><spage>13369</spage><epage>13378</epage><pages>13369-13378</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>The palladium‐catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C−Br bond versus C−OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene (Xantphos) vs. 1,1′‐bis(diphenylphosphino)ferrocene (DPPF)] and the solvent (toluene vs. DMSO). The respective ligand and solvent effects are rationalized by DFT calculations. In contrast, the monodentate ligands BuPAd2 and tBu3P prefer the selective C−Br bond activation and are solvent insensitive.
Keep control: Palladium‐catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The influencing effects of different solvents (polar vs. non‐polar) and ligands (e.g., monodentate vs. bidentate) on the chemoselectivety is discussed based on experimental observations as well as DFT calculations (see scheme; Xantphos=4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene, DPPF=1,1′‐bis(diphenylphosphino)ferrocene).</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28650074</pmid><doi>10.1002/chem.201702015</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-6622-3328</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | bromoaryl triflates carbonylation Carbonyls Chemistry chemoselectivity Ligands Palladium solvent effects Solvents Toluene |
| title | Ligand‐ and Solvent‐Tuned Chemoselective Carbonylation of Bromoaryl Triflates |
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