Uncatalyzed Hydrogenation of First-Row Main Group Multiple Bonds
Room temperature hydrogenation of an SIDep‐stabilized diboryne (SIDep=1,3‐bis(diethylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene) and a cAAC‐supported diboracumulene (cAAC=1‐(2,6‐diisopropylphenyl)‐3,3,5,5‐tetramethylpyrrolidin‐2‐ylidene) provided the first selective route to the corresponding 1,2‐dihydro...
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| Veröffentlicht in: | Chemistry : a European journal 2016-11, Vol.22 (48), p.17169-17172 |
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| container_issue | 48 |
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| container_title | Chemistry : a European journal |
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| creator | Arrowsmith, Merle Böhnke, Julian Braunschweig, Holger Celik, Mehmet Ali Dellermann, Theresa Hammond, Kai |
| description | Room temperature hydrogenation of an SIDep‐stabilized diboryne (SIDep=1,3‐bis(diethylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene) and a cAAC‐supported diboracumulene (cAAC=1‐(2,6‐diisopropylphenyl)‐3,3,5,5‐tetramethylpyrrolidin‐2‐ylidene) provided the first selective route to the corresponding 1,2‐dihydrodiborenes. DFT calculations showed an overall exothermic (ΔG=19.4 kcal mol−1) two‐step asynchronous H2 addition mechanism proceeding via a bridging hydride.
No catalyst needed: Two new carbene‐stabilized 1,2‐dihydrodiborenes have been synthesized by the direct and selective monohydrogenation of boron–boron multiple bonds under mild conditions. Theoretical calculations show a two‐step asynchronous H2 addition mechanism proceeding via a bridging hydride. |
| doi_str_mv | 10.1002/chem.201604094 |
| format | Article |
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No catalyst needed: Two new carbene‐stabilized 1,2‐dihydrodiborenes have been synthesized by the direct and selective monohydrogenation of boron–boron multiple bonds under mild conditions. Theoretical calculations show a two‐step asynchronous H2 addition mechanism proceeding via a bridging hydride.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201604094</identifier><identifier>PMID: 27685839</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Boron ; Bridging ; carbenes ; Catalysts ; Chemical bonds ; Chemistry ; diborenes ; Hydrides ; Hydrogenation ; main-group chemistry ; Mathematical analysis ; reaction mechanism ; Synthesis (chemistry)</subject><ispartof>Chemistry : a European journal, 2016-11, Vol.22 (48), p.17169-17172</ispartof><rights>2016 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6154-3462a274820a3875e29900e7128572371f8e1a303dd59720bfbaf28de11c46b03</citedby><cites>FETCH-LOGICAL-c6154-3462a274820a3875e29900e7128572371f8e1a303dd59720bfbaf28de11c46b03</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%2Fchem.201604094$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201604094$$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/27685839$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Arrowsmith, Merle</creatorcontrib><creatorcontrib>Böhnke, Julian</creatorcontrib><creatorcontrib>Braunschweig, Holger</creatorcontrib><creatorcontrib>Celik, Mehmet Ali</creatorcontrib><creatorcontrib>Dellermann, Theresa</creatorcontrib><creatorcontrib>Hammond, Kai</creatorcontrib><title>Uncatalyzed Hydrogenation of First-Row Main Group Multiple Bonds</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Room temperature hydrogenation of an SIDep‐stabilized diboryne (SIDep=1,3‐bis(diethylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene) and a cAAC‐supported diboracumulene (cAAC=1‐(2,6‐diisopropylphenyl)‐3,3,5,5‐tetramethylpyrrolidin‐2‐ylidene) provided the first selective route to the corresponding 1,2‐dihydrodiborenes. DFT calculations showed an overall exothermic (ΔG=19.4 kcal mol−1) two‐step asynchronous H2 addition mechanism proceeding via a bridging hydride.
No catalyst needed: Two new carbene‐stabilized 1,2‐dihydrodiborenes have been synthesized by the direct and selective monohydrogenation of boron–boron multiple bonds under mild conditions. Theoretical calculations show a two‐step asynchronous H2 addition mechanism proceeding via a bridging hydride.</description><subject>Boron</subject><subject>Bridging</subject><subject>carbenes</subject><subject>Catalysts</subject><subject>Chemical bonds</subject><subject>Chemistry</subject><subject>diborenes</subject><subject>Hydrides</subject><subject>Hydrogenation</subject><subject>main-group chemistry</subject><subject>Mathematical analysis</subject><subject>reaction mechanism</subject><subject>Synthesis (chemistry)</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqNkU1L60AUhge5ovVj61ICd-Mm9cz3zE4t2gqtQlFcDtNkco2mmTqToPXXG6mWiwt1deDwvM_h8CJ0gKGPAchxdu_mfQJYAAPNNlAPc4JTKgX_g3rdRqaCU72NdmJ8AAAtKN1C20QKxRXVPXRyW2e2sdXy1eXJaJkH_8_Vtil9nfgiuShDbNKpf04mtqyTYfDtIpm0VVMuKpec-TqPe2izsFV0-x9zF91enN8MRun4eng5OB2nmcCcpZQJYolkioClSnJHtAZwEhPFJaESF8phS4HmOdeSwKyY2YKo3GGcMTEDuouOVt5F8E-ti42ZlzFzVWVr59tosBKMCwIgfoFSLgRjmnXo3y_og29D3T1isKacgKTd_I5SjMnuMlEd1V9RWfAxBleYRSjnNiwNBvNelnkvy6zL6gKHH9p2Nnf5Gv9spwP0CnguK7f8QWcGo_PJ__J0lS1j417WWRsejZBUcnN3NTSYj8XNmZ6aKX0DQF2rTQ</recordid><startdate>20161121</startdate><enddate>20161121</enddate><creator>Arrowsmith, Merle</creator><creator>Böhnke, Julian</creator><creator>Braunschweig, Holger</creator><creator>Celik, Mehmet Ali</creator><creator>Dellermann, Theresa</creator><creator>Hammond, Kai</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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></search><sort><creationdate>20161121</creationdate><title>Uncatalyzed Hydrogenation of First-Row Main Group Multiple Bonds</title><author>Arrowsmith, Merle ; Böhnke, Julian ; Braunschweig, Holger ; Celik, Mehmet Ali ; Dellermann, Theresa ; Hammond, Kai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6154-3462a274820a3875e29900e7128572371f8e1a303dd59720bfbaf28de11c46b03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Boron</topic><topic>Bridging</topic><topic>carbenes</topic><topic>Catalysts</topic><topic>Chemical bonds</topic><topic>Chemistry</topic><topic>diborenes</topic><topic>Hydrides</topic><topic>Hydrogenation</topic><topic>main-group chemistry</topic><topic>Mathematical analysis</topic><topic>reaction mechanism</topic><topic>Synthesis (chemistry)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Arrowsmith, Merle</creatorcontrib><creatorcontrib>Böhnke, Julian</creatorcontrib><creatorcontrib>Braunschweig, Holger</creatorcontrib><creatorcontrib>Celik, Mehmet Ali</creatorcontrib><creatorcontrib>Dellermann, Theresa</creatorcontrib><creatorcontrib>Hammond, Kai</creatorcontrib><collection>Istex</collection><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>Arrowsmith, Merle</au><au>Böhnke, Julian</au><au>Braunschweig, Holger</au><au>Celik, Mehmet Ali</au><au>Dellermann, Theresa</au><au>Hammond, Kai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Uncatalyzed Hydrogenation of First-Row Main Group Multiple Bonds</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-11-21</date><risdate>2016</risdate><volume>22</volume><issue>48</issue><spage>17169</spage><epage>17172</epage><pages>17169-17172</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Room temperature hydrogenation of an SIDep‐stabilized diboryne (SIDep=1,3‐bis(diethylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene) and a cAAC‐supported diboracumulene (cAAC=1‐(2,6‐diisopropylphenyl)‐3,3,5,5‐tetramethylpyrrolidin‐2‐ylidene) provided the first selective route to the corresponding 1,2‐dihydrodiborenes. DFT calculations showed an overall exothermic (ΔG=19.4 kcal mol−1) two‐step asynchronous H2 addition mechanism proceeding via a bridging hydride.
No catalyst needed: Two new carbene‐stabilized 1,2‐dihydrodiborenes have been synthesized by the direct and selective monohydrogenation of boron–boron multiple bonds under mild conditions. Theoretical calculations show a two‐step asynchronous H2 addition mechanism proceeding via a bridging hydride.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27685839</pmid><doi>10.1002/chem.201604094</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Boron Bridging carbenes Catalysts Chemical bonds Chemistry diborenes Hydrides Hydrogenation main-group chemistry Mathematical analysis reaction mechanism Synthesis (chemistry) |
| title | Uncatalyzed Hydrogenation of First-Row Main Group Multiple Bonds |
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