Bis(pyrazolyl)methane Copper Complexes as Robust and Efficient Catalysts for Sonogashira Couplings
A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of several iodoarenes with terminal alkynes such as phenylacetylene, propargyl benzyl ether, and (tert‐butyl‐dimethyl)silylacetylene. These reactions proceed with CuCl2·2H2O...
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| Veröffentlicht in: | European journal of organic chemistry 2015-12, Vol.2015 (34), p.7475-7483 |
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| container_title | European journal of organic chemistry |
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| creator | Moegling, Julian Benischke, Andreas D. Hammann, Jeffrey M. Vepřek, Nynke A. Zoller, Florian Rendenbach, Bettina Hoffmann, Alexander Sievers, Holger Schuster, Michael Knochel, Paul Herres-Pawlis, Sonja |
| description | A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of several iodoarenes with terminal alkynes such as phenylacetylene, propargyl benzyl ether, and (tert‐butyl‐dimethyl)silylacetylene. These reactions proceed with CuCl2·2H2O (10 mol‐%) under aerobic conditions and the corresponding chelate ligand (10 mol‐%), with its tailored facial coordination mode, is crucial for the success of the reaction. The coupling can also be carried out in water with liquid aryl halides and a phase‐transfer catalyst.
A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of various iodoarenes with terminal alkynes. The reactions proceed under aerobic conditions, which makes this system synthetically highly useful. For liquid electrophiles, a substitution of DMF with water is possible when a phase‐transfer catalyst is provided. |
| doi_str_mv | 10.1002/ejoc.201501117 |
| format | Article |
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A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of various iodoarenes with terminal alkynes. The reactions proceed under aerobic conditions, which makes this system synthetically highly useful. For liquid electrophiles, a substitution of DMF with water is possible when a phase‐transfer catalyst is provided.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201501117</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkynes ; C-C coupling ; Copper ; Cross-coupling ; Homogeneous catalysis ; N ligands</subject><ispartof>European journal of organic chemistry, 2015-12, Vol.2015 (34), p.7475-7483</ispartof><rights>Copyright © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4257-4556ae369b2e99b862dfecc9c9780f855a5332dce04ae3dd8f35bed994d6920f3</citedby><cites>FETCH-LOGICAL-c4257-4556ae369b2e99b862dfecc9c9780f855a5332dce04ae3dd8f35bed994d6920f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201501117$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201501117$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Moegling, Julian</creatorcontrib><creatorcontrib>Benischke, Andreas D.</creatorcontrib><creatorcontrib>Hammann, Jeffrey M.</creatorcontrib><creatorcontrib>Vepřek, Nynke A.</creatorcontrib><creatorcontrib>Zoller, Florian</creatorcontrib><creatorcontrib>Rendenbach, Bettina</creatorcontrib><creatorcontrib>Hoffmann, Alexander</creatorcontrib><creatorcontrib>Sievers, Holger</creatorcontrib><creatorcontrib>Schuster, Michael</creatorcontrib><creatorcontrib>Knochel, Paul</creatorcontrib><creatorcontrib>Herres-Pawlis, Sonja</creatorcontrib><title>Bis(pyrazolyl)methane Copper Complexes as Robust and Efficient Catalysts for Sonogashira Couplings</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of several iodoarenes with terminal alkynes such as phenylacetylene, propargyl benzyl ether, and (tert‐butyl‐dimethyl)silylacetylene. These reactions proceed with CuCl2·2H2O (10 mol‐%) under aerobic conditions and the corresponding chelate ligand (10 mol‐%), with its tailored facial coordination mode, is crucial for the success of the reaction. The coupling can also be carried out in water with liquid aryl halides and a phase‐transfer catalyst.
A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of various iodoarenes with terminal alkynes. The reactions proceed under aerobic conditions, which makes this system synthetically highly useful. For liquid electrophiles, a substitution of DMF with water is possible when a phase‐transfer catalyst is provided.</description><subject>Alkynes</subject><subject>C-C coupling</subject><subject>Copper</subject><subject>Cross-coupling</subject><subject>Homogeneous catalysis</subject><subject>N ligands</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkDtPwzAUhSMEEs-VORILDCnXdhzHI0QtD1W8EWyWk1xDShoHOxWEX0-qIsTGdO7wfedKJwj2CYwIAD3GmS1GFAgHQohYC7YISBlBImF9uGMWR0Sy581g2_sZAMgkIVtBflr5w7Z3-svWfX00x-5VNxhmtm3RDTFva_xEH2of3tl84btQN2U4NqYqKmy6MNOdrnvf-dBYF97bxr5o_1o5PbiLtq6aF78bbBhde9z7yZ3gcTJ-yM6j6fXZRXYyjYqYchHFnCcaWSJzilLmaUJLg0UhCylSMCnnmjNGywIhHrCyTA3jOZZSxmUiKRi2Exyseltn3xfoOzWzC9cMLxURXFAAIuKBGq2owlnvHRrVumquXa8IqOWOarmj-t1xEORK-Khq7P-h1fjyOvvrRiu38h1-_rravalEMMHV09WZytJJevMkqLpl3xLzh2M</recordid><startdate>201512</startdate><enddate>201512</enddate><creator>Moegling, Julian</creator><creator>Benischke, Andreas D.</creator><creator>Hammann, Jeffrey M.</creator><creator>Vepřek, Nynke A.</creator><creator>Zoller, Florian</creator><creator>Rendenbach, Bettina</creator><creator>Hoffmann, Alexander</creator><creator>Sievers, Holger</creator><creator>Schuster, Michael</creator><creator>Knochel, Paul</creator><creator>Herres-Pawlis, Sonja</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201512</creationdate><title>Bis(pyrazolyl)methane Copper Complexes as Robust and Efficient Catalysts for Sonogashira Couplings</title><author>Moegling, Julian ; Benischke, Andreas D. ; Hammann, Jeffrey M. ; Vepřek, Nynke A. ; Zoller, Florian ; Rendenbach, Bettina ; Hoffmann, Alexander ; Sievers, Holger ; Schuster, Michael ; Knochel, Paul ; Herres-Pawlis, Sonja</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4257-4556ae369b2e99b862dfecc9c9780f855a5332dce04ae3dd8f35bed994d6920f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkynes</topic><topic>C-C coupling</topic><topic>Copper</topic><topic>Cross-coupling</topic><topic>Homogeneous catalysis</topic><topic>N ligands</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moegling, Julian</creatorcontrib><creatorcontrib>Benischke, Andreas D.</creatorcontrib><creatorcontrib>Hammann, Jeffrey M.</creatorcontrib><creatorcontrib>Vepřek, Nynke A.</creatorcontrib><creatorcontrib>Zoller, Florian</creatorcontrib><creatorcontrib>Rendenbach, Bettina</creatorcontrib><creatorcontrib>Hoffmann, Alexander</creatorcontrib><creatorcontrib>Sievers, Holger</creatorcontrib><creatorcontrib>Schuster, Michael</creatorcontrib><creatorcontrib>Knochel, Paul</creatorcontrib><creatorcontrib>Herres-Pawlis, Sonja</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moegling, Julian</au><au>Benischke, Andreas D.</au><au>Hammann, Jeffrey M.</au><au>Vepřek, Nynke A.</au><au>Zoller, Florian</au><au>Rendenbach, Bettina</au><au>Hoffmann, Alexander</au><au>Sievers, Holger</au><au>Schuster, Michael</au><au>Knochel, Paul</au><au>Herres-Pawlis, Sonja</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bis(pyrazolyl)methane Copper Complexes as Robust and Efficient Catalysts for Sonogashira Couplings</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2015-12</date><risdate>2015</risdate><volume>2015</volume><issue>34</issue><spage>7475</spage><epage>7483</epage><pages>7475-7483</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of several iodoarenes with terminal alkynes such as phenylacetylene, propargyl benzyl ether, and (tert‐butyl‐dimethyl)silylacetylene. These reactions proceed with CuCl2·2H2O (10 mol‐%) under aerobic conditions and the corresponding chelate ligand (10 mol‐%), with its tailored facial coordination mode, is crucial for the success of the reaction. The coupling can also be carried out in water with liquid aryl halides and a phase‐transfer catalyst.
A series of bis(pyrazolyl)methane copper complexes were found to catalyze a fast palladium‐free Sonogashira coupling reaction of various iodoarenes with terminal alkynes. The reactions proceed under aerobic conditions, which makes this system synthetically highly useful. For liquid electrophiles, a substitution of DMF with water is possible when a phase‐transfer catalyst is provided.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201501117</doi><tpages>9</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkynes C-C coupling Copper Cross-coupling Homogeneous catalysis N ligands |
| title | Bis(pyrazolyl)methane Copper Complexes as Robust and Efficient Catalysts for Sonogashira Couplings |
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