“Inverse” Frustrated Lewis Pairs: An Inverse FLP Approach to the Catalytic Metal Free Hydrogenation of Ketones
For the first time have boron‐containing weak Lewis acids been demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the hydrogenation of ketones to alcohols. Combining the organosuperbase (pyrr)3P=NtBu with the Lewis acid 9‐(4‐CF3‐C6H4)‐BBN generated an “inverse” FLP cata...
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| Veröffentlicht in: | Chemistry : a European journal 2018-11, Vol.24 (62), p.16526-16531 |
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| container_title | Chemistry : a European journal |
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| creator | Mummadi, Suresh Brar, Amandeep Wang, Guoqiang Kenefake, Dustin Diaz, Rony Unruh, Daniel K. Li, Shuhua Krempner, Clemens |
| description | For the first time have boron‐containing weak Lewis acids been demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the hydrogenation of ketones to alcohols. Combining the organosuperbase (pyrr)3P=NtBu with the Lewis acid 9‐(4‐CF3‐C6H4)‐BBN generated an “inverse” FLP catalyst capable of hydrogenating a range of aliphatic and aromatic ketones including N‐, O‐ and S‐functionalized substrates and bio‐mass derived ethyl levulinate. Initial computational and experimental studies indicate the mechanism of catalytic hydrogenation with “inverse” FLPs to be different from conventional FLP catalysts that contain strong Lewis acids such as B(C6F5)3.
For the first time, boron‐containing weak Lewis acids have demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the highly selective hydrogenation of ketones to alcohols. The “inverse” FLP system (pyrr)3P=NtBu/9‐(4‐CF3‐C6H4)‐BBN hydrogenates a range of aliphatic and aromatic ketones including N‐, O‐ and S‐functionalized substrates and bio‐mass derived ethyl levulinate. |
| doi_str_mv | 10.1002/chem.201804370 |
| format | Article |
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For the first time, boron‐containing weak Lewis acids have demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the highly selective hydrogenation of ketones to alcohols. The “inverse” FLP system (pyrr)3P=NtBu/9‐(4‐CF3‐C6H4)‐BBN hydrogenates a range of aliphatic and aromatic ketones including N‐, O‐ and S‐functionalized substrates and bio‐mass derived ethyl levulinate.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201804370</identifier><identifier>PMID: 30168212</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Acids ; Alcohols ; Aliphatic compounds ; Boron ; Catalysis ; Catalysts ; catalytic hydrogenation ; Chemistry ; Computer applications ; frustrated Lewis Pair ; hydrogen cleavage ; Hydrogenation ; Ketones ; Lewis acid ; metal-free ; Substrates</subject><ispartof>Chemistry : a European journal, 2018-11, Vol.24 (62), p.16526-16531</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4130-d3cd5bfd0684c1aa6a6ffc38e5226ac0bcd72f7fd2789f2843438318d852303e3</citedby><cites>FETCH-LOGICAL-c4130-d3cd5bfd0684c1aa6a6ffc38e5226ac0bcd72f7fd2789f2843438318d852303e3</cites><orcidid>0000-0003-2596-591X</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.201804370$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201804370$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30168212$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mummadi, Suresh</creatorcontrib><creatorcontrib>Brar, Amandeep</creatorcontrib><creatorcontrib>Wang, Guoqiang</creatorcontrib><creatorcontrib>Kenefake, Dustin</creatorcontrib><creatorcontrib>Diaz, Rony</creatorcontrib><creatorcontrib>Unruh, Daniel K.</creatorcontrib><creatorcontrib>Li, Shuhua</creatorcontrib><creatorcontrib>Krempner, Clemens</creatorcontrib><title>“Inverse” Frustrated Lewis Pairs: An Inverse FLP Approach to the Catalytic Metal Free Hydrogenation of Ketones</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>For the first time have boron‐containing weak Lewis acids been demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the hydrogenation of ketones to alcohols. Combining the organosuperbase (pyrr)3P=NtBu with the Lewis acid 9‐(4‐CF3‐C6H4)‐BBN generated an “inverse” FLP catalyst capable of hydrogenating a range of aliphatic and aromatic ketones including N‐, O‐ and S‐functionalized substrates and bio‐mass derived ethyl levulinate. Initial computational and experimental studies indicate the mechanism of catalytic hydrogenation with “inverse” FLPs to be different from conventional FLP catalysts that contain strong Lewis acids such as B(C6F5)3.
For the first time, boron‐containing weak Lewis acids have demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the highly selective hydrogenation of ketones to alcohols. The “inverse” FLP system (pyrr)3P=NtBu/9‐(4‐CF3‐C6H4)‐BBN hydrogenates a range of aliphatic and aromatic ketones including N‐, O‐ and S‐functionalized substrates and bio‐mass derived ethyl levulinate.</description><subject>Acids</subject><subject>Alcohols</subject><subject>Aliphatic compounds</subject><subject>Boron</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>catalytic hydrogenation</subject><subject>Chemistry</subject><subject>Computer applications</subject><subject>frustrated Lewis Pair</subject><subject>hydrogen cleavage</subject><subject>Hydrogenation</subject><subject>Ketones</subject><subject>Lewis acid</subject><subject>metal-free</subject><subject>Substrates</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkU1vEzEQhi0EomnhyhFZ4sJlg-3ZDy-3KGqailTtAc6WY4_JVpt1sL1UufWHwJ_rL8FVQpG49DRzeObRq3kJecfZlDMmPpkNbqeCcclKaNgLMuGV4AU0dfWSTFhbNkVdQXtCTmO8ZYy1NcBrcgKM11JwMSHh4f7X5fATQ8SH-990EcaYgk5o6QrvukhvdBfiZzob6JGii9UNne12wWuzocnTtEE610n3-9QZeoV5yxpEutzb4L_joFPnB-od_YLJDxjfkFdO9xHfHucZ-bY4_zpfFqvri8v5bFWYkgMrLBhbrZ1ltSwN17rWtXMGJFZC1NqwtbGNcI2zopGtE7KEEiRwaWUlgAHCGfl48OasP0aMSW27aLDv9YB-jEqwVuY_AecZ_fAfeuvHMOR0SrS8kWUpWsjU9ECZ4GMM6NQudFsd9ooz9diGemxDPbWRD94fteN6i_YJ__v-DLQH4K7rcf-MTs2X51f_5H8Ar0SXVg</recordid><startdate>20181107</startdate><enddate>20181107</enddate><creator>Mummadi, Suresh</creator><creator>Brar, Amandeep</creator><creator>Wang, Guoqiang</creator><creator>Kenefake, Dustin</creator><creator>Diaz, Rony</creator><creator>Unruh, Daniel K.</creator><creator>Li, Shuhua</creator><creator>Krempner, Clemens</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/0000-0003-2596-591X</orcidid></search><sort><creationdate>20181107</creationdate><title>“Inverse” Frustrated Lewis Pairs: An Inverse FLP Approach to the Catalytic Metal Free Hydrogenation of Ketones</title><author>Mummadi, Suresh ; Brar, Amandeep ; Wang, Guoqiang ; Kenefake, Dustin ; Diaz, Rony ; Unruh, Daniel K. ; Li, Shuhua ; Krempner, Clemens</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4130-d3cd5bfd0684c1aa6a6ffc38e5226ac0bcd72f7fd2789f2843438318d852303e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acids</topic><topic>Alcohols</topic><topic>Aliphatic compounds</topic><topic>Boron</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>catalytic hydrogenation</topic><topic>Chemistry</topic><topic>Computer applications</topic><topic>frustrated Lewis Pair</topic><topic>hydrogen cleavage</topic><topic>Hydrogenation</topic><topic>Ketones</topic><topic>Lewis acid</topic><topic>metal-free</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mummadi, Suresh</creatorcontrib><creatorcontrib>Brar, Amandeep</creatorcontrib><creatorcontrib>Wang, Guoqiang</creatorcontrib><creatorcontrib>Kenefake, Dustin</creatorcontrib><creatorcontrib>Diaz, Rony</creatorcontrib><creatorcontrib>Unruh, Daniel K.</creatorcontrib><creatorcontrib>Li, Shuhua</creatorcontrib><creatorcontrib>Krempner, Clemens</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>Mummadi, Suresh</au><au>Brar, Amandeep</au><au>Wang, Guoqiang</au><au>Kenefake, Dustin</au><au>Diaz, Rony</au><au>Unruh, Daniel K.</au><au>Li, Shuhua</au><au>Krempner, Clemens</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>“Inverse” Frustrated Lewis Pairs: An Inverse FLP Approach to the Catalytic Metal Free Hydrogenation of Ketones</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2018-11-07</date><risdate>2018</risdate><volume>24</volume><issue>62</issue><spage>16526</spage><epage>16531</epage><pages>16526-16531</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>For the first time have boron‐containing weak Lewis acids been demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the hydrogenation of ketones to alcohols. Combining the organosuperbase (pyrr)3P=NtBu with the Lewis acid 9‐(4‐CF3‐C6H4)‐BBN generated an “inverse” FLP catalyst capable of hydrogenating a range of aliphatic and aromatic ketones including N‐, O‐ and S‐functionalized substrates and bio‐mass derived ethyl levulinate. Initial computational and experimental studies indicate the mechanism of catalytic hydrogenation with “inverse” FLPs to be different from conventional FLP catalysts that contain strong Lewis acids such as B(C6F5)3.
For the first time, boron‐containing weak Lewis acids have demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the highly selective hydrogenation of ketones to alcohols. The “inverse” FLP system (pyrr)3P=NtBu/9‐(4‐CF3‐C6H4)‐BBN hydrogenates a range of aliphatic and aromatic ketones including N‐, O‐ and S‐functionalized substrates and bio‐mass derived ethyl levulinate.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30168212</pmid><doi>10.1002/chem.201804370</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-2596-591X</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Acids Alcohols Aliphatic compounds Boron Catalysis Catalysts catalytic hydrogenation Chemistry Computer applications frustrated Lewis Pair hydrogen cleavage Hydrogenation Ketones Lewis acid metal-free Substrates |
| title | “Inverse” Frustrated Lewis Pairs: An Inverse FLP Approach to the Catalytic Metal Free Hydrogenation of Ketones |
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