NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature

Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has be...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-01, Vol.56 (4), p.575-578
Main Authors: Hota, Pradip Kumar, Maji, Subir, Ahmed, Jasimuddin, Rajendran, N. M, Mandal, Swadhin K
Format: Article
Language:English
Subjects:
Amides
Chemical reactions
Dehydration
Nitriles
Room temperature
Siloxanes
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Summary:Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study. An abnormal NHC acts as an efficient catalyst for catalytic silylative dehydration of primary amides to nitriles under ambient conditions.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc08413d