Premium
Straightforward Iron‐Catalyzed Synthesis of Nitriles by Dehydration of Primary Amides
Author(s) -
Enthaler Stephan
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100754
Subject(s) - chemistry , dehydration , reagent , catalysis , trimethylsilyl , solvent , primary (astronomy) , organic chemistry , medicinal chemistry , biochemistry , physics , astronomy
Abstract In the present study, the iron‐catalyzed dehydration of a range of amides to the corresponding nitriles by using N ‐methyl‐ N ‐(trimethylsilyl)trifluoroacetamide (MSTFA) as the dehydration reagent has been explored. After investigating different reaction parameters (e.g., iron source, solvent, catalyst loading) with FeCl 2 · 4H 2 O, an excellent and easily accessible precatalyst was found. The obtained system (5.0 mol‐% [Fe], 3.0 equiv. MSTFA) was highly active and dehydrated a broad scope of amides selectively to the corresponding nitriles under mild reaction conditions (THF, 70 °C) within two hours (yields: >99 %, selectivities: >99 %).