Synthesis of α‐Fluoroamides with a C–F Quaternary Stereogenic Center by Electrophilic Fluorination: One‐Pot Four‐Component Strategy. Issue 22 (23rd May 2019)

• Record Type: Journal Article
• Authors: Krishna Swaroop, Desireddy; Ravi Kumar, Nagiri; Reddy, Narra Srikanth; Punna, Nagender; Jagadeesh Babu, Nanubolu; Narsaiah, Banda
• Is Part Of: European journal of organic chemistry. Issue 22(2019)
• Page Start: 3654
• Page End: 3657
• Publication Date: 2019-05-23
• Subjects: Fluorination -- Fluoroamides -- Isocyanides -- Multicomponent reactions -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900482
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : We have successfully developed a one‐pot four‐component strategy for the synthesis of α‐fluoroamides via a 3‐fluoro 4H–pyran key intermediate. The reaction proceeds under simple and metal‐free conditions and produced the corresponding products with high diastereoselectivty. Irrespective of substrates, the reaction proceeds very smoothly. Fluorine plays a crucial role to deliver the desired α‐fluoroamides with a C–F quaternary center in excellent yields.