Scope and mechanism of nitrile dihydroboration mediated by a β-diketiminate manganese hydride catalyst
The manganese hydride dimer, [( 2,6-iPr 2 Ph BDI)Mn(μ-H)] 2 , was found to mediate nitrile dihydroboration, rendering it the first manganese catalyst for this transformation. Stoichiometric experiments revealed that benzonitrile insertion affords [( 2,6-iPr 2 Ph BDI)Mn(μ-NCHC 6 H 5 )] 2 en route to...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-04, Vol.56 (28), p.3959-3962 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Nguyen, Thao T Kim, Jun-Hyeong Kim, Suyeon Oh, Changjin Flores, Marco Groy, Thomas L Baik, Mu-Hyun Trovitch, Ryan J |
| description | The manganese hydride dimer, [(
2,6-iPr
2
Ph
BDI)Mn(μ-H)]
2
, was found to mediate nitrile dihydroboration, rendering it the first manganese catalyst for this transformation. Stoichiometric experiments revealed that benzonitrile insertion affords [(
2,6-iPr
2
Ph
BDI)Mn(μ-NCHC
6
H
5
)]
2
en route to
N
,
N
-diborylamine formation. Density functional theory calculations reveal the precise mechanism and demonstrate that catalysis is promoted by monomeric species.
Nitrile insertion allows for manganese-catalyzed nitrile dihydroboration at 80 °C. |
| doi_str_mv | 10.1039/c9cc09921b |
| format | Article |
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2,6-iPr
2
Ph
BDI)Mn(μ-H)]
2
, was found to mediate nitrile dihydroboration, rendering it the first manganese catalyst for this transformation. Stoichiometric experiments revealed that benzonitrile insertion affords [(
2,6-iPr
2
Ph
BDI)Mn(μ-NCHC
6
H
5
)]
2
en route to
N
,
N
-diborylamine formation. Density functional theory calculations reveal the precise mechanism and demonstrate that catalysis is promoted by monomeric species.
Nitrile insertion allows for manganese-catalyzed nitrile dihydroboration at 80 °C.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc09921b</identifier><identifier>PMID: 32149290</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Benzonitrile ; Catalysis ; Catalysts ; Crystallography ; Density functional theory ; Dimers ; Hydrides ; Manganese</subject><ispartof>Chemical communications (Cambridge, England), 2020-04, Vol.56 (28), p.3959-3962</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-88b280e157364f231dae6f3aa0d9fa30f1e6a83b0924a77ae7140a0b3aecd1803</citedby><cites>FETCH-LOGICAL-c363t-88b280e157364f231dae6f3aa0d9fa30f1e6a83b0924a77ae7140a0b3aecd1803</cites><orcidid>0000-0003-4935-6780 ; 0000-0002-8832-8187 ; 0000-0003-4139-7094 ; 0000-0001-7747-5475 ; 0000-0002-5545-7441</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32149290$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nguyen, Thao T</creatorcontrib><creatorcontrib>Kim, Jun-Hyeong</creatorcontrib><creatorcontrib>Kim, Suyeon</creatorcontrib><creatorcontrib>Oh, Changjin</creatorcontrib><creatorcontrib>Flores, Marco</creatorcontrib><creatorcontrib>Groy, Thomas L</creatorcontrib><creatorcontrib>Baik, Mu-Hyun</creatorcontrib><creatorcontrib>Trovitch, Ryan J</creatorcontrib><title>Scope and mechanism of nitrile dihydroboration mediated by a β-diketiminate manganese hydride catalyst</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The manganese hydride dimer, [(
2,6-iPr
2
Ph
BDI)Mn(μ-H)]
2
, was found to mediate nitrile dihydroboration, rendering it the first manganese catalyst for this transformation. Stoichiometric experiments revealed that benzonitrile insertion affords [(
2,6-iPr
2
Ph
BDI)Mn(μ-NCHC
6
H
5
)]
2
en route to
N
,
N
-diborylamine formation. Density functional theory calculations reveal the precise mechanism and demonstrate that catalysis is promoted by monomeric species.
Nitrile insertion allows for manganese-catalyzed nitrile dihydroboration at 80 °C.</description><subject>Benzonitrile</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Crystallography</subject><subject>Density functional theory</subject><subject>Dimers</subject><subject>Hydrides</subject><subject>Manganese</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90b1O3TAUB3CrKuql0KV7K6MuCClgx_mwxxKVDwmJgVZii07sE65pEqd2MuS1eJA-E75coFIHvNiyfz46_puQz5wdcybUiVZaM6VS3rwju1wUWZJn8vb9Zp2rpBRZviIfQ7hncfBcfiArkfJMpYrtkrsb7UakMBjao17DYENPXUsHO3nbITV2vRjvGudhsm6IyFiY0NBmoUD_PiTG_sbJ9naIu7SH4Q4GDEg3t6xBqmGCbgnTPtlpoQv46XneI7_OfvysLpKr6_PL6vtVokUhpkTKJpUMeV7GZ7Sp4AawaAUAM6oFwVqOBUjRMJVmUJaAJc8YsEYAasMlE3vkcFt39O7PjGGqexs0dl1sy82hTkWZ5ywvGY_023_03s1-iN1FJQvFsrKQUR1tlfYuBI9tPXrbg19qzupN_HWlquop_tOIvz6XnJuY1Ct9yTuCgy3wQb-e_vu_ejRtNF_eMuIRrcmWQQ</recordid><startdate>20200411</startdate><enddate>20200411</enddate><creator>Nguyen, Thao T</creator><creator>Kim, Jun-Hyeong</creator><creator>Kim, Suyeon</creator><creator>Oh, Changjin</creator><creator>Flores, Marco</creator><creator>Groy, Thomas L</creator><creator>Baik, Mu-Hyun</creator><creator>Trovitch, Ryan J</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4935-6780</orcidid><orcidid>https://orcid.org/0000-0002-8832-8187</orcidid><orcidid>https://orcid.org/0000-0003-4139-7094</orcidid><orcidid>https://orcid.org/0000-0001-7747-5475</orcidid><orcidid>https://orcid.org/0000-0002-5545-7441</orcidid></search><sort><creationdate>20200411</creationdate><title>Scope and mechanism of nitrile dihydroboration mediated by a β-diketiminate manganese hydride catalyst</title><author>Nguyen, Thao T ; Kim, Jun-Hyeong ; Kim, Suyeon ; Oh, Changjin ; Flores, Marco ; Groy, Thomas L ; Baik, Mu-Hyun ; Trovitch, Ryan J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-88b280e157364f231dae6f3aa0d9fa30f1e6a83b0924a77ae7140a0b3aecd1803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Benzonitrile</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Crystallography</topic><topic>Density functional theory</topic><topic>Dimers</topic><topic>Hydrides</topic><topic>Manganese</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nguyen, Thao T</creatorcontrib><creatorcontrib>Kim, Jun-Hyeong</creatorcontrib><creatorcontrib>Kim, Suyeon</creatorcontrib><creatorcontrib>Oh, Changjin</creatorcontrib><creatorcontrib>Flores, Marco</creatorcontrib><creatorcontrib>Groy, Thomas L</creatorcontrib><creatorcontrib>Baik, Mu-Hyun</creatorcontrib><creatorcontrib>Trovitch, Ryan J</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nguyen, Thao T</au><au>Kim, Jun-Hyeong</au><au>Kim, Suyeon</au><au>Oh, Changjin</au><au>Flores, Marco</au><au>Groy, Thomas L</au><au>Baik, Mu-Hyun</au><au>Trovitch, Ryan J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Scope and mechanism of nitrile dihydroboration mediated by a β-diketiminate manganese hydride catalyst</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-04-11</date><risdate>2020</risdate><volume>56</volume><issue>28</issue><spage>3959</spage><epage>3962</epage><pages>3959-3962</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The manganese hydride dimer, [(
2,6-iPr
2
Ph
BDI)Mn(μ-H)]
2
, was found to mediate nitrile dihydroboration, rendering it the first manganese catalyst for this transformation. Stoichiometric experiments revealed that benzonitrile insertion affords [(
2,6-iPr
2
Ph
BDI)Mn(μ-NCHC
6
H
5
)]
2
en route to
N
,
N
-diborylamine formation. Density functional theory calculations reveal the precise mechanism and demonstrate that catalysis is promoted by monomeric species.
Nitrile insertion allows for manganese-catalyzed nitrile dihydroboration at 80 °C.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32149290</pmid><doi>10.1039/c9cc09921b</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-4935-6780</orcidid><orcidid>https://orcid.org/0000-0002-8832-8187</orcidid><orcidid>https://orcid.org/0000-0003-4139-7094</orcidid><orcidid>https://orcid.org/0000-0001-7747-5475</orcidid><orcidid>https://orcid.org/0000-0002-5545-7441</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-04, Vol.56 (28), p.3959-3962 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2375505701 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Benzonitrile Catalysis Catalysts Crystallography Density functional theory Dimers Hydrides Manganese |
| title | Scope and mechanism of nitrile dihydroboration mediated by a β-diketiminate manganese hydride catalyst |
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