Manganese-catalyzed selective C-H activation and deuteration by means of a catalytic transient directing group strategy

A novel manganese-catalyzed C-H activation methodology for selective hydrogen isotope exchange of benzaldehydes is presented. Using D 2 O as a cheap and convenient source of deuterium, the reaction proceeds with excellent functional group tolerance. High ortho -selectivity is achieved in the presenc...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-01, Vol.57 (9), p.1137-114
Main Authors: Kopf, Sara, Neumann, Helfried, Beller, Matthias
Format: Article
Language:English
Subjects:
Amines
Deuteration
Deuterium
Functional groups
Hydrogen isotopes
Manganese
Selectivity
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Summary:A novel manganese-catalyzed C-H activation methodology for selective hydrogen isotope exchange of benzaldehydes is presented. Using D 2 O as a cheap and convenient source of deuterium, the reaction proceeds with excellent functional group tolerance. High ortho -selectivity is achieved in the presence of catalytic amounts of specific amines, which in situ form a transient directing group. A shortcut to ortho -deuterated aldehydes: a catalytic directing group enables the manganese-catalyzed C-H activation and deuteration of benzaldehydes in one step.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc07675a