Nickel-Catalyzed Conversion of Amides to Carboxylic Acids.
Org Lett
; 22(7): 2833-2837, 2020 04 03.
Article
in En
| MEDLINE
| ID: mdl-32208664
ABSTRACT
We report the conversion of amides to carboxylic acids using nonprecious metal catalysis. The methodology strategically employs a nickel-catalyzed esterification using 2-(trimethylsilyl)ethanol, followed by a fluoride-mediated deprotection in a single-pot operation. This approach circumvents catalyst poisoning observed in attempts to directly hydrolyze amides using nickel catalysis. The selectivity and mildness of this transformation are shown through competition experiments and the net-hydrolysis of a complex valine-derived substrate. This strategy addresses a limitation in the field with regard to functional groups accessible from amides using transition metal-catalyzed C-N bond activation and should prove useful in synthetic applications.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Carboxylic Acids
/
Amides
/
Nickel
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2020
Document type:
Article
Affiliation country:
United States