Rhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisation
Pyridines are ubiquitous aromatic rings used in organic chemistry and are crucial elements of the drug discovery process. Herein we describe a new catalytic method that directly introduces a methyl group onto the aromatic ring; this new reaction is related to hydrogen borrowing, and is notable for i...
| Autors principals: | , , , , |
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| Format: | Journal article |
| Idioma: | English |
| Publicat: |
Royal Society of Chemistry
2020
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| _version_ | 1826279653141118976 |
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| author | Grosavu, A Hepburn, H Bailey, E Lindsay-Scott, P Donohoe, T |
| author_facet | Grosavu, A Hepburn, H Bailey, E Lindsay-Scott, P Donohoe, T |
| author_sort | Grosavu, A |
| collection | OXFORD |
| description | Pyridines are ubiquitous aromatic rings used in organic chemistry and are crucial elements of the drug discovery process. Herein we describe a new catalytic method that directly introduces a methyl group onto the aromatic ring; this new reaction is related to hydrogen borrowing, and is notable for its use of the feedstock chemicals methanol and formaldehyde as the key reagents. Conceptually, the C-3/5 methylation of pyridines was accomplished by exploiting the interface between aromatic and non-aromatic compounds, and this allows an oscillating reactivity pattern to emerge whereby normally electrophilic aromatic compounds become nucleophilic in the reaction after activation by reduction. Thus, a set of C-4 functionalised pyridines can be mono or doubly methylated at the C-3/5 positions.
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| first_indexed | 2024-03-07T00:01:59Z |
| format | Journal article |
| id | oxford-uuid:764490ad-16f4-4c3d-89f3-addff0fcef29 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:01:59Z |
| publishDate | 2020 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:764490ad-16f4-4c3d-89f3-addff0fcef292022-03-26T20:14:44ZRhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisationJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:764490ad-16f4-4c3d-89f3-addff0fcef29EnglishSymplectic ElementsRoyal Society of Chemistry2020Grosavu, AHepburn, HBailey, ELindsay-Scott, PDonohoe, TPyridines are ubiquitous aromatic rings used in organic chemistry and are crucial elements of the drug discovery process. Herein we describe a new catalytic method that directly introduces a methyl group onto the aromatic ring; this new reaction is related to hydrogen borrowing, and is notable for its use of the feedstock chemicals methanol and formaldehyde as the key reagents. Conceptually, the C-3/5 methylation of pyridines was accomplished by exploiting the interface between aromatic and non-aromatic compounds, and this allows an oscillating reactivity pattern to emerge whereby normally electrophilic aromatic compounds become nucleophilic in the reaction after activation by reduction. Thus, a set of C-4 functionalised pyridines can be mono or doubly methylated at the C-3/5 positions. |
| spellingShingle | Grosavu, A Hepburn, H Bailey, E Lindsay-Scott, P Donohoe, T Rhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisation |
| title | Rhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisation |
| title_full | Rhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisation |
| title_fullStr | Rhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisation |
| title_full_unstemmed | Rhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisation |
| title_short | Rhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisation |
| title_sort | rhodium catalysed c 3 5 methylation of pyridines using temporary dearomatisation |
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