Sc(OTf)3‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction

• Published in: European journal of organic chemistry Vol. 27; no. 31
• Main Authors: Gogula, Sailam Sri, Prasanna, Dasari Vijaya, Sridhar, B., Lincoln, Ch. Abraham, Reddy, P. Muralidhar, Reddy, B. V. Subba
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 19.08.2024
• Subjects: 3-substituted lawsones; Chemical synthesis; C−H insertion reactions; Diazo compounds; ninhydrin; Scandium triflate; Substitutes; Toluene
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202400362

An efficient strategy has been developed for the synthesis of 3‐substituted lawsones using a catalytic amount of Sc(OTf)3 in toluene at −78 °C through a Buchner‐Curtius‐Schlotterbeck reaction. It is a versatile method to produce a large number of 3‐aryl, 3‐styryl, 3‐alkyl, and 3‐heteroaryl substituted lawsones under mild conditions. This is a first report on the synthesis of 3‐substituted lawsones in high yields with in short reaction times. An efficient method has been developed for the synthesis of 3‐substituted lawsones using 10 mol % Sc(OTf)3 in toluene at −78 °C through a Buchner‐Curtius‐Schlotterbeck reaction. This method is simple and convenient to the synthesis of pharmaceutically relevant 3‐substituted lawsones in high to excellent yields.