A method for the functionalization of the important bio-derived compound was developed in the ZIOC
The transformation of biomass derivatives into valuable products is one of the most important areas of green chemistry and sustainable development. In this context, one of the key compounds is 5-hydroxymethylfurfural (5-HMF), which is easily obtained from biological raw materials. Currently, the chemical transformations of 5-HMF and its derivatives are being actively studied as potential environmentally friendly approaches to the preparation of a wide range of organic compounds of various classes. However, one of the problems with the synthetic use of 5-HMF is that the introduction of substituents in the alpha position of its furan ring often proceeds with low atom-efficiency.
Researchers from the Laboratory of Metal Complex and Nanoscale Catalysts of the ZIOC proposed a method for the synthesis of 2-aryl and 2-hetaryl-substituted furans from readily available 5-HMF derivatives, which is characterized by 100% atom-efficiency. The reaction proceeds as [2+2+2] or [4+2] cycloaddition in the presence of metal catalysts or under photoredox catalysis conditions. It should be especially noted that the developed approach made it possible to obtain highly functionalized (hetero)aryl derivatives of furans, which are difficult to synthesize using previously known methods.
Leonid V. Romashov, Kirill S. Kozlov, Matvey K. Skorobogatko, Alexander Y. Kostyukovich, Valentine P. Ananikov Atom-economic Approach to the Synthesis of α-(Hetero)arylsubstituted Furan Derivatives from Biomass Chem Asian J. 2022, 17, e202101227. DOI: 10.1002/asia.202101227.