Premium
Synthesis of α‐Fluoroamides with a C–F Quaternary Stereogenic Center by Electrophilic Fluorination: One‐Pot Four‐Component Strategy
Author(s) -
Krishna Swaroop Desireddy,
Ravi Kumar Nagiri,
Reddy Narra Srikanth,
Pungender,
Jagadeesh Babu Nanubolu,
Narsaiah Banda
Publication year - 2019
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.201900482
Subject(s) - stereocenter , chemistry , isocyanide , electrophilic fluorination , acetylenedicarboxylate , electronegativity , electrophile , fluorine , component (thermodynamics) , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , catalysis , enantioselective synthesis , physics , thermodynamics
An efficient method for the synthesis of α‐fluoroamides having C–F quaternary stereogenic center was achieved by a one‐pot four‐component strategy under mild reaction conditions. A variety of α‐fluoroamides was synthesized by using 1,3‐dicarbonyl, isocyanide, acetylenedicarboxylate and N ‐fluorobenzenesulfonimide (NFSI) systems with good to excellent yields up to 93 %. The current protocol proceeds through the unstable 3‐fluoro 4 H ‐pyran intermediate, which is key for the reaction and further it can be hydrolyzed due to the high electronegativity of the fluorine atom to produce the desired α‐fluoroamides.