A New Class of Free Radical Alkylation Reagents: Fluoroalkyl Sulfones


Hu Jinbo, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, has been working on novel fluoroalkylation reactions based on fluorine-containing sulfur-containing systems (such as fluoroalkyl sulfone, fluoroalkyl sulfoxide imine, fluoroalkyl sulfide, etc.) Studies on fluoroalkylation reactions and systematic work have been done (for a recent review, see: Chem. Rev. 2015, 115, 765-825). Recently, under the joint efforts of Professor Hu Jinbo and his research fellow Ph.D. student Rong Jian and associate researcher Ni Chuanfa, a new synthetic use of fluoroalkyl sulfone has been successfully developed as a free radical fluoroalkylation reagent. . Using photo-oxidation-reduction catalysis, this mild reaction condition, they achieved radical fluoroalkylation of the template substrate isonitrile by selective reduction of heteroaryl fluoroalkyl sulfone.

Compared with the existing free radical fluoroalkylation methods, the fluoroalkyl sulfone reagents used in this method are not only easy to obtain raw materials, but also easy to operate, and the fluoroalkyl end can be flexible and suitable for a variety of fluoroalkylation reactions. It is expected to find applications in the introduction of functionalized fluoroalkyl groups. This method not only expands the synthesis and application of fluoroalkyl sulfone, but also finds a new type of practical and uniform precursor for various fluoroalkyl radicals.

The results of this study were published in German Applied Chemistry (Angew. Chem. Int. Ed. 2016, 55, 2743-2747) and were selected as internal seals for highlights.