A β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compounds
An oxidation/substitution strategy for the synthesis of silicon analogues of classical organic carbonyl compounds is reported, by making use of a novel β-diketiminate-supported sila-acyl chloride-the first example of such a compound isolated without the use of a stabilizing Lewis acid. Nucleophilic...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2018
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| _version_ | 1797052327171981312 |
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| author | Do, D Protchenko, A Ángeles Fuentes, M Hicks, J Kolychev, E Vasko, P Aldridge, S |
| author_facet | Do, D Protchenko, A Ángeles Fuentes, M Hicks, J Kolychev, E Vasko, P Aldridge, S |
| author_sort | Do, D |
| collection | OXFORD |
| description | An oxidation/substitution strategy for the synthesis of silicon analogues of classical organic carbonyl compounds is reported, by making use of a novel β-diketiminate-supported sila-acyl chloride-the first example of such a compound isolated without the use of a stabilizing Lewis acid. Nucleophilic substitution at the SiIV center allows direct access to the corresponding sila-aldehyde and sila-ester. An alternative approach utilizing the reverse order of synthetic steps is thwarted by the facile rearrangement of the corresponding SiII systems featuring either H or OR substituents. As such, the isolation of (N-nacnac)Si(O)Cl represents a key step forward in enabling the synthesis of sila-carbonyl compounds by a synthetic approach ubiquitous in organic chemistry. |
| first_indexed | 2024-03-06T18:30:30Z |
| format | Journal article |
| id | oxford-uuid:0978f446-dcf6-4fe8-9300-972285f36ba3 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:30:30Z |
| publishDate | 2018 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:0978f446-dcf6-4fe8-9300-972285f36ba32022-03-26T09:18:35ZA β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compoundsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:0978f446-dcf6-4fe8-9300-972285f36ba3EnglishSymplectic Elements at OxfordWiley2018Do, DProtchenko, AÁngeles Fuentes, MHicks, JKolychev, EVasko, PAldridge, SAn oxidation/substitution strategy for the synthesis of silicon analogues of classical organic carbonyl compounds is reported, by making use of a novel β-diketiminate-supported sila-acyl chloride-the first example of such a compound isolated without the use of a stabilizing Lewis acid. Nucleophilic substitution at the SiIV center allows direct access to the corresponding sila-aldehyde and sila-ester. An alternative approach utilizing the reverse order of synthetic steps is thwarted by the facile rearrangement of the corresponding SiII systems featuring either H or OR substituents. As such, the isolation of (N-nacnac)Si(O)Cl represents a key step forward in enabling the synthesis of sila-carbonyl compounds by a synthetic approach ubiquitous in organic chemistry. |
| spellingShingle | Do, D Protchenko, A Ángeles Fuentes, M Hicks, J Kolychev, E Vasko, P Aldridge, S A β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compounds |
| title | A β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compounds |
| title_full | A β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compounds |
| title_fullStr | A β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compounds |
| title_full_unstemmed | A β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compounds |
| title_short | A β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compounds |
| title_sort | β diketiminate stabilized sila acyl chloride systematic access to base stabilized silicon analogues of classical carbonyl compounds |
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