Manganese-catalysed C2 allylation and deuteration of indoles in water
Mn-catalysed C–H activation has emerged as a useful sustainable methodology for the formation of new C–C bonds. To date most of the protocols are described in organic solvents. Water as solvent, on the other hand, would be highly advantageous, but is often incompatible with organometallic chemistry....
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-12-01
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| Series: | Tetrahedron Green Chem |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2773223123000183 |
| _version_ | 1797342105751781376 |
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| author | Si Lok Ko Eimear Courtney Dr Mark Light Dr David Jones Dr Gerard P. McGlacken |
| author_facet | Si Lok Ko Eimear Courtney Dr Mark Light Dr David Jones Dr Gerard P. McGlacken |
| author_sort | Si Lok Ko |
| collection | DOAJ |
| description | Mn-catalysed C–H activation has emerged as a useful sustainable methodology for the formation of new C–C bonds. To date most of the protocols are described in organic solvents. Water as solvent, on the other hand, would be highly advantageous, but is often incompatible with organometallic chemistry. Herein, we describe the C–H activation of indoles using an unmodified, commercially available manganese catalyst in water. Two types of valuable allyl groups can be added and a good substrate scope is described. Substitution at the C-3 group is tolerated, allowing access to medicinally important frameworks, and the reaction works on a gram scale. Finally, harnessing the tolerance of water as the reaction medium, D2O can be used as an inexpensive source of deuterium for the C-2 labelling of indoles. |
| first_indexed | 2024-03-08T10:28:36Z |
| format | Article |
| id | doaj.art-777dde1d2a564fe59635ec294f14e0ae |
| institution | Directory Open Access Journal |
| issn | 2773-2231 |
| language | English |
| last_indexed | 2024-03-08T10:28:36Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Tetrahedron Green Chem |
| spelling | doaj.art-777dde1d2a564fe59635ec294f14e0ae2024-01-27T07:03:09ZengElsevierTetrahedron Green Chem2773-22312023-12-012100019Manganese-catalysed C2 allylation and deuteration of indoles in waterSi Lok Ko0Eimear Courtney1Dr Mark Light2Dr David Jones3Dr Gerard P. McGlacken4School of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, T12 YN60, Ireland; Department of Chemistry, EPSRC National Crystallography Service, University of Southampton, Highfield, Southampton, SO17 1BJ, United Kingdom; EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, United KingdomSchool of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, T12 YN60, Ireland; Department of Chemistry, EPSRC National Crystallography Service, University of Southampton, Highfield, Southampton, SO17 1BJ, United Kingdom; EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, United KingdomDepartment of Chemistry, EPSRC National Crystallography Service, University of Southampton, Highfield, Southampton, SO17 1BJ, United KingdomEaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, United KingdomCorresponding author.; School of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, T12 YN60, Ireland; Department of Chemistry, EPSRC National Crystallography Service, University of Southampton, Highfield, Southampton, SO17 1BJ, United Kingdom; EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, United KingdomMn-catalysed C–H activation has emerged as a useful sustainable methodology for the formation of new C–C bonds. To date most of the protocols are described in organic solvents. Water as solvent, on the other hand, would be highly advantageous, but is often incompatible with organometallic chemistry. Herein, we describe the C–H activation of indoles using an unmodified, commercially available manganese catalyst in water. Two types of valuable allyl groups can be added and a good substrate scope is described. Substitution at the C-3 group is tolerated, allowing access to medicinally important frameworks, and the reaction works on a gram scale. Finally, harnessing the tolerance of water as the reaction medium, D2O can be used as an inexpensive source of deuterium for the C-2 labelling of indoles.http://www.sciencedirect.com/science/article/pii/S2773223123000183C–H activationMn catalysisAqueous solventDeuterationGram-scale |
| spellingShingle | Si Lok Ko Eimear Courtney Dr Mark Light Dr David Jones Dr Gerard P. McGlacken Manganese-catalysed C2 allylation and deuteration of indoles in water Tetrahedron Green Chem C–H activation Mn catalysis Aqueous solvent Deuteration Gram-scale |
| title | Manganese-catalysed C2 allylation and deuteration of indoles in water |
| title_full | Manganese-catalysed C2 allylation and deuteration of indoles in water |
| title_fullStr | Manganese-catalysed C2 allylation and deuteration of indoles in water |
| title_full_unstemmed | Manganese-catalysed C2 allylation and deuteration of indoles in water |
| title_short | Manganese-catalysed C2 allylation and deuteration of indoles in water |
| title_sort | manganese catalysed c2 allylation and deuteration of indoles in water |
| topic | C–H activation Mn catalysis Aqueous solvent Deuteration Gram-scale |
| url | http://www.sciencedirect.com/science/article/pii/S2773223123000183 |
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