Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations
We report herein the exploitment of the partially fluorinated trifluoroethyl as precatalyst ligands in nickel-catalyzed Suzuki-type alkylation and fluoroalkylation coupling reactions. Compared with the [L n Ni II (aryl)(X)] precatalysts, the unique characters of bis-trifluoroethyl ligands imparted p...
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| Veröffentlicht in: | Chemical science (Cambridge) 2019-05, Vol.1 (2), p.5275-5282 |
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| creator | Yang, Yi Zhou, Qinghai Cai, Junjie Xue, Teng Liu, Yingle Jiang, Yan Su, Yumei Chung, Lungwa Vicic, David A |
| description | We report herein the exploitment of the partially fluorinated trifluoroethyl as precatalyst ligands in nickel-catalyzed Suzuki-type alkylation and fluoroalkylation coupling reactions. Compared with the [L
n
Ni
II
(aryl)(X)] precatalysts, the unique characters of bis-trifluoroethyl ligands imparted precatalyst [(bipy)Ni(CH
2
CF
3
)
2
] with bench-top stability, good solubilities in organic media and interesting catalytic activities. Preliminary mechanistic studies reveal that an eliminative extrusion of a vinylidene difluoride (VDF, CH
2
&z.dbd;CF
2
) mask from [(bipy)Ni(CH
2
CF
3
)
2
] is a critical step for the initiation of a catalytic reaction.
A bis-trifluoroethyl coordinated nickel/bipyridine complex has been developed as efficient precatalyst for diverse Suzuki-type alkylations which features unconventional precatalyst initiation mode. |
| doi_str_mv | 10.1039/c9sc00554d |
| format | Article |
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n
Ni
II
(aryl)(X)] precatalysts, the unique characters of bis-trifluoroethyl ligands imparted precatalyst [(bipy)Ni(CH
2
CF
3
)
2
] with bench-top stability, good solubilities in organic media and interesting catalytic activities. Preliminary mechanistic studies reveal that an eliminative extrusion of a vinylidene difluoride (VDF, CH
2
&z.dbd;CF
2
) mask from [(bipy)Ni(CH
2
CF
3
)
2
] is a critical step for the initiation of a catalytic reaction.
A bis-trifluoroethyl coordinated nickel/bipyridine complex has been developed as efficient precatalyst for diverse Suzuki-type alkylations which features unconventional precatalyst initiation mode.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c9sc00554d</identifier><identifier>PMID: 31191883</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chemistry ; INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY</subject><ispartof>Chemical science (Cambridge), 2019-05, Vol.1 (2), p.5275-5282</ispartof><rights>This journal is © The Royal Society of Chemistry 2019.</rights><rights>This journal is © The Royal Society of Chemistry 2019 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c519t-864a3ca2c54c21f12a3bcdb8e942c9c64c659cf9a4c6f3187cfac952a5191f283</citedby><cites>FETCH-LOGICAL-c519t-864a3ca2c54c21f12a3bcdb8e942c9c64c659cf9a4c6f3187cfac952a5191f283</cites><orcidid>0000-0001-6057-3378 ; 0000-0001-9460-7812 ; 0000000194607812 ; 0000000160573378</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6540912/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6540912/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31191883$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/1509518$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Yi</creatorcontrib><creatorcontrib>Zhou, Qinghai</creatorcontrib><creatorcontrib>Cai, Junjie</creatorcontrib><creatorcontrib>Xue, Teng</creatorcontrib><creatorcontrib>Liu, Yingle</creatorcontrib><creatorcontrib>Jiang, Yan</creatorcontrib><creatorcontrib>Su, Yumei</creatorcontrib><creatorcontrib>Chung, Lungwa</creatorcontrib><creatorcontrib>Vicic, David A</creatorcontrib><creatorcontrib>Lehigh Univ., Bethlehem, PA (United States)</creatorcontrib><title>Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>We report herein the exploitment of the partially fluorinated trifluoroethyl as precatalyst ligands in nickel-catalyzed Suzuki-type alkylation and fluoroalkylation coupling reactions. Compared with the [L
n
Ni
II
(aryl)(X)] precatalysts, the unique characters of bis-trifluoroethyl ligands imparted precatalyst [(bipy)Ni(CH
2
CF
3
)
2
] with bench-top stability, good solubilities in organic media and interesting catalytic activities. Preliminary mechanistic studies reveal that an eliminative extrusion of a vinylidene difluoride (VDF, CH
2
&z.dbd;CF
2
) mask from [(bipy)Ni(CH
2
CF
3
)
2
] is a critical step for the initiation of a catalytic reaction.
A bis-trifluoroethyl coordinated nickel/bipyridine complex has been developed as efficient precatalyst for diverse Suzuki-type alkylations which features unconventional precatalyst initiation mode.</description><subject>Chemistry</subject><subject>INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9ks1v1DAQxS0EolXphTvIcKqQAv5M40sltC0UqRKHwtnyTpysWa8dbKdq-teTknaBC3PxSO83b0Z6RuglJe8p4eoDqAyESCnaJ-iQEUGrWnL1dN8zcoCOc_5B5uKcSnb6HB1wShVtGn6I-ovbwUdXXOhx2Vhckuv8GFO0ZTN53Kc4DthkbPCQLJhi_JQL9q43ocUu4OBga321KHe2xdfj3bh1VZkGi43fTt4UF0N-gZ51xmd7_PAeoe-fLr6tLqurr5-_rD5eVSCpKlVTC8PBMJACGO0oM3wN7bqxSjBQUAuopYJOmbnpOG1OoTOgJDPzNO1Yw4_Q2eI7jOudbcGGkozXQ3I7kyYdjdP_KsFtdB9vdC0FUZTNBm8Xg5iL0xlcsbCBGIKFoqkkStL7LScPW1L8Odpc9M5lsN6bYOOYNeOCEME5JzP6bkEhxZyT7fa3UKLvE9Qrdb36neD5DL_--_o9-pjXDLxagJRhr_75ArP-5n-6HtqO_wLbg65w</recordid><startdate>20190528</startdate><enddate>20190528</enddate><creator>Yang, Yi</creator><creator>Zhou, Qinghai</creator><creator>Cai, Junjie</creator><creator>Xue, Teng</creator><creator>Liu, Yingle</creator><creator>Jiang, Yan</creator><creator>Su, Yumei</creator><creator>Chung, Lungwa</creator><creator>Vicic, David A</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>OTOTI</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-6057-3378</orcidid><orcidid>https://orcid.org/0000-0001-9460-7812</orcidid><orcidid>https://orcid.org/0000000194607812</orcidid><orcidid>https://orcid.org/0000000160573378</orcidid></search><sort><creationdate>20190528</creationdate><title>Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations</title><author>Yang, Yi ; Zhou, Qinghai ; Cai, Junjie ; Xue, Teng ; Liu, Yingle ; Jiang, Yan ; Su, Yumei ; Chung, Lungwa ; Vicic, David A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c519t-864a3ca2c54c21f12a3bcdb8e942c9c64c659cf9a4c6f3187cfac952a5191f283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Chemistry</topic><topic>INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Yi</creatorcontrib><creatorcontrib>Zhou, Qinghai</creatorcontrib><creatorcontrib>Cai, Junjie</creatorcontrib><creatorcontrib>Xue, Teng</creatorcontrib><creatorcontrib>Liu, Yingle</creatorcontrib><creatorcontrib>Jiang, Yan</creatorcontrib><creatorcontrib>Su, Yumei</creatorcontrib><creatorcontrib>Chung, Lungwa</creatorcontrib><creatorcontrib>Vicic, David A</creatorcontrib><creatorcontrib>Lehigh Univ., Bethlehem, PA (United States)</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>OSTI.GOV</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Yi</au><au>Zhou, Qinghai</au><au>Cai, Junjie</au><au>Xue, Teng</au><au>Liu, Yingle</au><au>Jiang, Yan</au><au>Su, Yumei</au><au>Chung, Lungwa</au><au>Vicic, David A</au><aucorp>Lehigh Univ., Bethlehem, PA (United States)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2019-05-28</date><risdate>2019</risdate><volume>1</volume><issue>2</issue><spage>5275</spage><epage>5282</epage><pages>5275-5282</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>We report herein the exploitment of the partially fluorinated trifluoroethyl as precatalyst ligands in nickel-catalyzed Suzuki-type alkylation and fluoroalkylation coupling reactions. Compared with the [L
n
Ni
II
(aryl)(X)] precatalysts, the unique characters of bis-trifluoroethyl ligands imparted precatalyst [(bipy)Ni(CH
2
CF
3
)
2
] with bench-top stability, good solubilities in organic media and interesting catalytic activities. Preliminary mechanistic studies reveal that an eliminative extrusion of a vinylidene difluoride (VDF, CH
2
&z.dbd;CF
2
) mask from [(bipy)Ni(CH
2
CF
3
)
2
] is a critical step for the initiation of a catalytic reaction.
A bis-trifluoroethyl coordinated nickel/bipyridine complex has been developed as efficient precatalyst for diverse Suzuki-type alkylations which features unconventional precatalyst initiation mode.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>31191883</pmid><doi>10.1039/c9sc00554d</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-6057-3378</orcidid><orcidid>https://orcid.org/0000-0001-9460-7812</orcidid><orcidid>https://orcid.org/0000000194607812</orcidid><orcidid>https://orcid.org/0000000160573378</orcidid><oa>free_for_read</oa></addata></record> |
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| title | Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations |
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