Spontaneous trans‐Selective Transfer Hydrogenation of Apolar Boron–Boron Double Bonds
The transfer hydrogenation of N‐heterocyclic carbene (NHC)‐supported diborenes with dimethylamine borane proceeds with high selectivity for the trans‐1,2‐dihydrodiboranes. DFT calculations, supported by kinetic studies and deuteration experiments, suggest a stepwise proton‐first‐hydride‐second react...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2019-07, Vol.58 (29), p.9782-9786 |
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| creator | Dömling, Michael Arrowsmith, Merle Schmidt, Uwe Werner, Luis Castro, Abril C. Jiménez‐Halla, J. Oscar C. Bertermann, Rüdiger Müssig, Jonas Prieschl, Dominic Braunschweig, Holger |
| description | The transfer hydrogenation of N‐heterocyclic carbene (NHC)‐supported diborenes with dimethylamine borane proceeds with high selectivity for the trans‐1,2‐dihydrodiboranes. DFT calculations, supported by kinetic studies and deuteration experiments, suggest a stepwise proton‐first‐hydride‐second reaction mechanism via an intermediate μ‐hydrodiboronium dimethylaminoborate ion pair.
Game of borons: The transfer hydrogenation of apolar cis‐ and trans‐diborenes with dimethylamine borane as the hydrogen source proceeds with high selectivity for the corresponding trans‐1,2‐dihydrodiboranes. DFT calculations, supported by kinetic data, reveal a new reaction mechanism proceeding via a proton‐first‐hydride‐second pathway through an intermediate μ‐hydrodiboronium aminoborate ion pair. |
| doi_str_mv | 10.1002/anie.201902656 |
| format | Article |
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Game of borons: The transfer hydrogenation of apolar cis‐ and trans‐diborenes with dimethylamine borane as the hydrogen source proceeds with high selectivity for the corresponding trans‐1,2‐dihydrodiboranes. DFT calculations, supported by kinetic data, reveal a new reaction mechanism proceeding via a proton‐first‐hydride‐second pathway through an intermediate μ‐hydrodiboronium aminoborate ion pair.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201902656</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>amine borane dehydrocoupling ; Boron ; Deuteration ; DFT mechanism ; diboranes ; diborene ; Hydrogenation ; Reaction mechanisms ; Selectivity ; transfer hydrogenation</subject><ispartof>Angewandte Chemie International Edition, 2019-07, Vol.58 (29), p.9782-9786</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4276-3f13295e319940f16945ae23ea92b12fb6e3a893fac42896a9521af74af049613</citedby><cites>FETCH-LOGICAL-c4276-3f13295e319940f16945ae23ea92b12fb6e3a893fac42896a9521af74af049613</cites><orcidid>0000-0003-1449-5932 ; 0000-0001-9264-1726</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%2Fanie.201902656$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201902656$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Dömling, Michael</creatorcontrib><creatorcontrib>Arrowsmith, Merle</creatorcontrib><creatorcontrib>Schmidt, Uwe</creatorcontrib><creatorcontrib>Werner, Luis</creatorcontrib><creatorcontrib>Castro, Abril C.</creatorcontrib><creatorcontrib>Jiménez‐Halla, J. Oscar C.</creatorcontrib><creatorcontrib>Bertermann, Rüdiger</creatorcontrib><creatorcontrib>Müssig, Jonas</creatorcontrib><creatorcontrib>Prieschl, Dominic</creatorcontrib><creatorcontrib>Braunschweig, Holger</creatorcontrib><title>Spontaneous trans‐Selective Transfer Hydrogenation of Apolar Boron–Boron Double Bonds</title><title>Angewandte Chemie International Edition</title><description>The transfer hydrogenation of N‐heterocyclic carbene (NHC)‐supported diborenes with dimethylamine borane proceeds with high selectivity for the trans‐1,2‐dihydrodiboranes. DFT calculations, supported by kinetic studies and deuteration experiments, suggest a stepwise proton‐first‐hydride‐second reaction mechanism via an intermediate μ‐hydrodiboronium dimethylaminoborate ion pair.
Game of borons: The transfer hydrogenation of apolar cis‐ and trans‐diborenes with dimethylamine borane as the hydrogen source proceeds with high selectivity for the corresponding trans‐1,2‐dihydrodiboranes. DFT calculations, supported by kinetic data, reveal a new reaction mechanism proceeding via a proton‐first‐hydride‐second pathway through an intermediate μ‐hydrodiboronium aminoborate ion pair.</description><subject>amine borane dehydrocoupling</subject><subject>Boron</subject><subject>Deuteration</subject><subject>DFT mechanism</subject><subject>diboranes</subject><subject>diborene</subject><subject>Hydrogenation</subject><subject>Reaction mechanisms</subject><subject>Selectivity</subject><subject>transfer hydrogenation</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAUhS0EEqWwMkdiYUnxT-LEYymFVqpgaBmYLDe9RqlSO9gpqFsfAYk37JPgEgQSC9O5uvrO1T0HoXOCewRjeqVMCT2KicCUp_wAdUhKScyyjB2GOWEszvKUHKMT75eBz3PMO-hpWlvTKAN27aPGKeN32_cpVFA05StEs_1Gg4tGm4Wzz2BUU1oTWR31a1spF11bZ81u-_Gl0Y1dzysIS7Pwp-hIq8rD2bd20ePtcDYYxZOHu_GgP4mLhGY8ZpowKlJgRIgEa8JFkiqgDJSgc0L1nANTuWBaBT4XXImQSuksURonghPWRZft3drZlzX4Rq5KX0BVtaEkpYwShrPQQBdd_EGXdu1M-C5QPMFZRgUPVK-lCme9d6Bl7cqVchtJsNw3LfdNy5-mg0G0hreygs0_tOzfj4e_3k_0OoNp</recordid><startdate>20190715</startdate><enddate>20190715</enddate><creator>Dömling, Michael</creator><creator>Arrowsmith, Merle</creator><creator>Schmidt, Uwe</creator><creator>Werner, Luis</creator><creator>Castro, Abril C.</creator><creator>Jiménez‐Halla, J. Oscar C.</creator><creator>Bertermann, Rüdiger</creator><creator>Müssig, Jonas</creator><creator>Prieschl, Dominic</creator><creator>Braunschweig, Holger</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1449-5932</orcidid><orcidid>https://orcid.org/0000-0001-9264-1726</orcidid></search><sort><creationdate>20190715</creationdate><title>Spontaneous trans‐Selective Transfer Hydrogenation of Apolar Boron–Boron Double Bonds</title><author>Dömling, Michael ; Arrowsmith, Merle ; Schmidt, Uwe ; Werner, Luis ; Castro, Abril C. ; Jiménez‐Halla, J. Oscar C. ; Bertermann, Rüdiger ; Müssig, Jonas ; Prieschl, Dominic ; Braunschweig, Holger</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4276-3f13295e319940f16945ae23ea92b12fb6e3a893fac42896a9521af74af049613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>amine borane dehydrocoupling</topic><topic>Boron</topic><topic>Deuteration</topic><topic>DFT mechanism</topic><topic>diboranes</topic><topic>diborene</topic><topic>Hydrogenation</topic><topic>Reaction mechanisms</topic><topic>Selectivity</topic><topic>transfer hydrogenation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dömling, Michael</creatorcontrib><creatorcontrib>Arrowsmith, Merle</creatorcontrib><creatorcontrib>Schmidt, Uwe</creatorcontrib><creatorcontrib>Werner, Luis</creatorcontrib><creatorcontrib>Castro, Abril C.</creatorcontrib><creatorcontrib>Jiménez‐Halla, J. Oscar C.</creatorcontrib><creatorcontrib>Bertermann, Rüdiger</creatorcontrib><creatorcontrib>Müssig, Jonas</creatorcontrib><creatorcontrib>Prieschl, Dominic</creatorcontrib><creatorcontrib>Braunschweig, Holger</creatorcontrib><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dömling, Michael</au><au>Arrowsmith, Merle</au><au>Schmidt, Uwe</au><au>Werner, Luis</au><au>Castro, Abril C.</au><au>Jiménez‐Halla, J. Oscar C.</au><au>Bertermann, Rüdiger</au><au>Müssig, Jonas</au><au>Prieschl, Dominic</au><au>Braunschweig, Holger</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Spontaneous trans‐Selective Transfer Hydrogenation of Apolar Boron–Boron Double Bonds</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2019-07-15</date><risdate>2019</risdate><volume>58</volume><issue>29</issue><spage>9782</spage><epage>9786</epage><pages>9782-9786</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The transfer hydrogenation of N‐heterocyclic carbene (NHC)‐supported diborenes with dimethylamine borane proceeds with high selectivity for the trans‐1,2‐dihydrodiboranes. DFT calculations, supported by kinetic studies and deuteration experiments, suggest a stepwise proton‐first‐hydride‐second reaction mechanism via an intermediate μ‐hydrodiboronium dimethylaminoborate ion pair.
Game of borons: The transfer hydrogenation of apolar cis‐ and trans‐diborenes with dimethylamine borane as the hydrogen source proceeds with high selectivity for the corresponding trans‐1,2‐dihydrodiboranes. DFT calculations, supported by kinetic data, reveal a new reaction mechanism proceeding via a proton‐first‐hydride‐second pathway through an intermediate μ‐hydrodiboronium aminoborate ion pair.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.201902656</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-1449-5932</orcidid><orcidid>https://orcid.org/0000-0001-9264-1726</orcidid><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | amine borane dehydrocoupling Boron Deuteration DFT mechanism diboranes diborene Hydrogenation Reaction mechanisms Selectivity transfer hydrogenation |
| title | Spontaneous trans‐Selective Transfer Hydrogenation of Apolar Boron–Boron Double Bonds |
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