New visible light organo(metal)-photocatalyzed fluoroalkylsulfanylation (RFS-) and fluoroalkylselenolation (RFSe-) reactions of organic substrates

Abstract

The fluoroalkylsulfanyl (RFS-) and fluoroalkylselenolyl (RFSe-) groups are becoming increasingly ubiquitous moieties in synthetic organic transformations on account of their relevance in areas ranging from medicinal chemistry to agrochemistry. For achieving such synthetic functionalities, different approaches have been conceived, such as the indirect fluoroalkylation reactions of sulfides and selenides. More recently, the direct-one-pot incorporation of these groups (i.e.: RFS- and RFSe-) has allowed for the late-stage functionalization of biological relevant substrates, which permits achieving synthetic protocols in the presence of other sensitive functional groups. In this venue, visible-light photocatalytic strategies are playing a fundamental role, as being environmentally friendly and easy to implement. This review article will explore visible light photocatalytic strategies to directly incorporate RFCY- groups (RF = CF2H, CF3, CnF2n+1, n > 1; Y = S, Se) into organic substrates and their reaction mechanisms. Section 1 will discuss the new examples on photocatalytic methods for the introduction of fluoroalkylsulfanyl (RFS-) groups, while Section 2 will focus on the most recent photocatalyzed fluoroalkylselenolation (RFSe-) strategies. A guidance to an abbreviated summary of the known and reviewed photocatalytic methods available for the introduction of RFS- and RFSe- groups is presented in two figures for researchers to put into perspective the new advancements herein informed. Discussion of the mechanisms for such transformations and further considerations for prospective photocatalyzed incorporations of these groups onto unexplored families of organic compounds will be discussed.