Carboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pair
<p>We report on the reactivity of isocyanates towards tris(pentafluorophenyl)borane which was found to result in the 1,2-carboboration of the isocyanate C=O bond. The resulting six-membered heterocyclic compounds can be rationalized as adducts of imino-boranes with isocyanates and react accord...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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Royal Society of Chemistry
2019
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| _version_ | 1826261325707214848 |
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| author | Mehta, M Goicoechea, J |
| author_facet | Mehta, M Goicoechea, J |
| author_sort | Mehta, M |
| collection | OXFORD |
| description | <p>We report on the reactivity of isocyanates towards tris(pentafluorophenyl)borane which was found to result in the 1,2-carboboration of the isocyanate C=O bond. The resulting six-membered heterocyclic compounds can be rationalized as adducts of imino-boranes with isocyanates and react accordingly, allowing for the dissociative displacement of the trapped isocyanate moiety in a series of exchange reactions. Related carboelementation reactions with the heavier group 13 analogues, Al(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> and Ga(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>, result in a dimerization of the carboboration products to afford eight-membered heterocycles.</p> |
| first_indexed | 2024-03-06T19:19:37Z |
| format | Journal article |
| id | oxford-uuid:199ff5d7-9119-40b4-8c0a-9221fc01f0d8 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:19:37Z |
| publishDate | 2019 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:199ff5d7-9119-40b4-8c0a-9221fc01f0d82022-03-26T10:49:57ZCarboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pairJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:199ff5d7-9119-40b4-8c0a-9221fc01f0d8EnglishSymplectic Elements at OxfordRoyal Society of Chemistry2019Mehta, MGoicoechea, J<p>We report on the reactivity of isocyanates towards tris(pentafluorophenyl)borane which was found to result in the 1,2-carboboration of the isocyanate C=O bond. The resulting six-membered heterocyclic compounds can be rationalized as adducts of imino-boranes with isocyanates and react accordingly, allowing for the dissociative displacement of the trapped isocyanate moiety in a series of exchange reactions. Related carboelementation reactions with the heavier group 13 analogues, Al(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> and Ga(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>, result in a dimerization of the carboboration products to afford eight-membered heterocycles.</p> |
| spellingShingle | Mehta, M Goicoechea, J Carboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pair |
| title | Carboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pair |
| title_full | Carboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pair |
| title_fullStr | Carboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pair |
| title_full_unstemmed | Carboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pair |
| title_short | Carboboration of isocyanates with tris(pentafluorophenyl)borane and evidence for dissociative FLP chemistry of an acid–base pair |
| title_sort | carboboration of isocyanates with tris pentafluorophenyl borane and evidence for dissociative flp chemistry of an acid base pair |
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