Manganese-catalysed C2 allylation and deuteration of indoles in water
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. 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.
Aqueous solvent, C–H activation, Deuteration, Gram-scale, Mn catalysis
Ko, Si Lok
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Courtney, Eimear
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Light, Dr Mark
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Jones, Dr David
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McGlacken, Dr Gerard P.
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5 August 2023
Ko, Si Lok
a2347aec-9696-494a-96a5-68028c7d09cf
Courtney, Eimear
8550e42b-898c-43a6-9b1c-2e7ae7f61c75
Light, Dr Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Jones, Dr David
47582c51-3751-4fc6-9355-444ccd33dc2b
McGlacken, Dr Gerard P.
487172f9-c842-41e3-8666-c9e0b7d0facc
Ko, Si Lok, Courtney, Eimear, Light, Dr Mark, Jones, Dr David and McGlacken, Dr Gerard P.
(2023)
Manganese-catalysed C2 allylation and deuteration of indoles in water.
Tetrahedron Green Chem, 2, [100019].
(doi:10.1016/j.tgchem.2023.100019).
Abstract
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.
Text
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More information
Accepted/In Press date: 12 July 2023
e-pub ahead of print date: 16 July 2023
Published date: 5 August 2023
Keywords:
Aqueous solvent, C–H activation, Deuteration, Gram-scale, Mn catalysis
Identifiers
Local EPrints ID: 491145
URI: http://eprints.soton.ac.uk/id/eprint/491145
PURE UUID: eeb6bbff-0f54-4a8c-b2ea-cf889da31f61
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Date deposited: 13 Jun 2024 16:44
Last modified: 14 Jun 2024 01:36
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Contributors
Author:
Si Lok Ko
Author:
Eimear Courtney
Author:
Dr David Jones
Author:
Dr Gerard P. McGlacken
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