Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis.
The application of an iridium-catalyzed hydrogen borrowing process to enable the formation of α-branched ketones with higher alcohols is described. In order to facilitate this reaction, ortho-disubstituted phenyl and cyclopropyl ketones were recognized as crucial structural motifs for C-C bond forma...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
American Chemical Society
2015
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| _version_ | 1797105180564520960 |
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| author | Frost, J Cheong, C Akhtar, W Caputo, D Stevenson, N Donohoe, T |
| author_facet | Frost, J Cheong, C Akhtar, W Caputo, D Stevenson, N Donohoe, T |
| author_sort | Frost, J |
| collection | OXFORD |
| description | The application of an iridium-catalyzed hydrogen borrowing process to enable the formation of α-branched ketones with higher alcohols is described. In order to facilitate this reaction, ortho-disubstituted phenyl and cyclopropyl ketones were recognized as crucial structural motifs for C-C bond formation. Having optimized the key catalysis step, the ortho-disubstituted phenyl products could be further manipulated by a retro-Friedel-Crafts acylation reaction to produce synthetically useful carboxylic acid derivatives. In contrast, the cyclopropyl ketones underwent homoconjugate addition with several nucleophiles to provide further functionalized branched ketone products. |
| first_indexed | 2024-03-07T06:43:47Z |
| format | Journal article |
| id | oxford-uuid:fa318189-0412-4a07-967e-fb27177bf34d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:43:47Z |
| publishDate | 2015 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:fa318189-0412-4a07-967e-fb27177bf34d2022-03-27T13:03:46ZStrategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:fa318189-0412-4a07-967e-fb27177bf34dEnglishSymplectic Elements at OxfordAmerican Chemical Society2015Frost, JCheong, CAkhtar, WCaputo, DStevenson, NDonohoe, TThe application of an iridium-catalyzed hydrogen borrowing process to enable the formation of α-branched ketones with higher alcohols is described. In order to facilitate this reaction, ortho-disubstituted phenyl and cyclopropyl ketones were recognized as crucial structural motifs for C-C bond formation. Having optimized the key catalysis step, the ortho-disubstituted phenyl products could be further manipulated by a retro-Friedel-Crafts acylation reaction to produce synthetically useful carboxylic acid derivatives. In contrast, the cyclopropyl ketones underwent homoconjugate addition with several nucleophiles to provide further functionalized branched ketone products. |
| spellingShingle | Frost, J Cheong, C Akhtar, W Caputo, D Stevenson, N Donohoe, T Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis. |
| title | Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis. |
| title_full | Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis. |
| title_fullStr | Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis. |
| title_full_unstemmed | Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis. |
| title_short | Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis. |
| title_sort | strategic application and transformation of ortho disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis |
| work_keys_str_mv | AT frostj strategicapplicationandtransformationoforthodisubstitutedphenylandcyclopropylketonestoexpandthescopeofhydrogenborrowingcatalysis AT cheongc strategicapplicationandtransformationoforthodisubstitutedphenylandcyclopropylketonestoexpandthescopeofhydrogenborrowingcatalysis AT akhtarw strategicapplicationandtransformationoforthodisubstitutedphenylandcyclopropylketonestoexpandthescopeofhydrogenborrowingcatalysis AT caputod strategicapplicationandtransformationoforthodisubstitutedphenylandcyclopropylketonestoexpandthescopeofhydrogenborrowingcatalysis AT stevensonn strategicapplicationandtransformationoforthodisubstitutedphenylandcyclopropylketonestoexpandthescopeofhydrogenborrowingcatalysis AT donohoet strategicapplicationandtransformationoforthodisubstitutedphenylandcyclopropylketonestoexpandthescopeofhydrogenborrowingcatalysis |