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Manganese-Pincer-Catalyzed Nitrile Hydration, α-Deuteration, and α-Deuterated Amide Formation via Metal Ligand Cooperation.
- Source :
-
ACS catalysis [ACS Catal] 2021 Aug 20; Vol. 11 (16), pp. 10239-10245. Date of Electronic Publication: 2021 Aug 03. - Publication Year :
- 2021
-
Abstract
- A simple and efficient system for the hydration and α-deuteration of nitriles to form amides, α-deuterated nitriles, and α-deuterated amides catalyzed by a single pincer complex of the earth-abundant manganese capable of metal-ligand cooperation is reported. The reaction is selective and tolerates a wide range of functional groups, giving the corresponding amides in moderate to good yields. Changing the solvent from tert -butanol to toluene and using D <subscript>2</subscript> O results in formation of α-deuterated nitriles in high selectivity. Moreover, α-deuterated amides can be obtained in one step directly from nitriles and D <subscript>2</subscript> O in THF. Preliminary mechanistic studies suggest the transformations contributing toward activation of the nitriles via a metal-ligand cooperative pathway, generating the manganese ketimido and enamido pincer complexes as the key intermediates for further transformations.<br />Competing Interests: The authors declare no competing financial interest.<br /> (© 2021 The Authors. Published by American Chemical Society.)
Details
- Language :
- English
- ISSN :
- 2155-5435
- Volume :
- 11
- Issue :
- 16
- Database :
- MEDLINE
- Journal :
- ACS catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 34476112
- Full Text :
- https://doi.org/10.1021/acscatal.1c01748