Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H-B(dan) as a B(dan) electrophile
H-B(dan) was demonstrated to serve as a B(dan) electrophile, despite its highly diminished boron-Lewis acidity, leading to direct and transition metal-free approach to R-B(dan) of high synthetic utility upon treatment with Grignard reagents. Iterative cross-coupling of 5-bromo-2-pyridyl-B(dan), synt...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-06, Vol.56 (47), p.6388-6391 |
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creator | Li, Jialun Seki, Michinari Kamio, Shintaro Yoshida, Hiroto |
description | H-B(dan) was demonstrated to serve as a B(dan) electrophile, despite its highly diminished boron-Lewis acidity, leading to direct and transition metal-free approach to R-B(dan) of high synthetic utility upon treatment with Grignard reagents. Iterative cross-coupling of 5-bromo-2-pyridyl-B(dan), synthesized by the present method, was also achieved.
H-B(dan) serves as a B(dan) electrophile to give directly R-B(dan) by the reaction with Grignard reagents under transition metal-free conditions. |
doi_str_mv | 10.1039/d0cc02560g |
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H-B(dan) serves as a B(dan) electrophile to give directly R-B(dan) by the reaction with Grignard reagents under transition metal-free conditions.</description><subject>Boron</subject><subject>Cross coupling</subject><subject>Naphthalene</subject><subject>Reagents</subject><subject>Transition metals</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90UFPHCEUB3BiatRuvfReM00vaop9wDDLeGvXqk1MetHE2-TJPFzMDDOF2UO_fVl3axMP5QLh_fgHeIy9F3AmQNVfWrAWpK7gcYcdCFWVXJfm_s16rWs-V6XeZ29TeoI8hDZ7bF9JVQNIdcCm24gh-ckPoehpwo67SFR8O24xnHAfUt7qfHgsIqF9VuvKeRFwXE5L7CgQF58Nbz32PuA0nJwX13xzvMBU4DaqoI7sFIdx6Tt6x3YddokOt_OM3V1-v11c85ufVz8WX2-4LWU9cZJzLaiyNVELWgKaOTpyCEpKVZFR1lmFNFeY32idcRZqJbWw1YNSGoyaseNN7hiHXytKU9P7ZKnrMNCwSo0sQUBtTI6bsU-v6NOwiiHfLishSpMT1-p0o2wcUorkmjH6HuPvRkCz7kVzAYvFcy-uMj7aRq4eempf6N_Pz-DjBsRkX6r_mtmMrcvmw_-M-gOVDZal</recordid><startdate>20200614</startdate><enddate>20200614</enddate><creator>Li, Jialun</creator><creator>Seki, Michinari</creator><creator>Kamio, Shintaro</creator><creator>Yoshida, Hiroto</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/0000-0001-6890-4397</orcidid></search><sort><creationdate>20200614</creationdate><title>Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H-B(dan) as a B(dan) electrophile</title><author>Li, Jialun ; Seki, Michinari ; Kamio, Shintaro ; Yoshida, Hiroto</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-e2751e6c9eed0520a87afefa032236e83cfc3ae73a734cf8fc093251c6b335083</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Boron</topic><topic>Cross coupling</topic><topic>Naphthalene</topic><topic>Reagents</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jialun</creatorcontrib><creatorcontrib>Seki, Michinari</creatorcontrib><creatorcontrib>Kamio, Shintaro</creatorcontrib><creatorcontrib>Yoshida, Hiroto</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>Li, Jialun</au><au>Seki, Michinari</au><au>Kamio, Shintaro</au><au>Yoshida, Hiroto</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H-B(dan) as a B(dan) electrophile</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-06-14</date><risdate>2020</risdate><volume>56</volume><issue>47</issue><spage>6388</spage><epage>6391</epage><pages>6388-6391</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>H-B(dan) was demonstrated to serve as a B(dan) electrophile, despite its highly diminished boron-Lewis acidity, leading to direct and transition metal-free approach to R-B(dan) of high synthetic utility upon treatment with Grignard reagents. Iterative cross-coupling of 5-bromo-2-pyridyl-B(dan), synthesized by the present method, was also achieved.
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source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
subjects | Boron Cross coupling Naphthalene Reagents Transition metals |
title | Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H-B(dan) as a B(dan) electrophile |
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