Abstract
Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly and straightforward pathways for the construction of C-C and C-heteroatom bonds. In this review, we emphasize the recent synthetic advances of late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagent and its applications to the synthesis of new arylated bioactive heterocyclic compounds.
Highlights
Late-stage diversification strategies that are based on heteroaromatic frameworks that contain multiple reactive sites are challenging and attractive for use in drug discovery [1,2,3]
While various reviews on C–H functionalization of heteroarenes have been already published [18,19,20,21,22], they are mainly focused on transition metal catalysis
In the quest for mild and sustainable late-stage functionalization, transition-metal-free diversification appears as a rewarding tool to build new functionalized heteroarene derivatives onto their established bioactive framework [23,24,25,26,27,28,29,30,31,32,33,34,35]
Summary
Late-stage diversification strategies that are based on heteroaromatic frameworks that contain multiple reactive sites are challenging and attractive for use in drug discovery [1,2,3]. Recent progress in this area has been achieved including selective C-H and N-H arylations of heteroarenes using non-toxic and easy-to-handle diaryliodonium salts as aromatic electrophiles [39,40,41,42]. This review provides an overview of the recent developments and early examples of arylating heteroarenes under metal-free conditions using acyclic diaryliodonium salts as coupling partners. Diaryliodonium salts viable reagents and led tive transfer of the sterically less hindered or electron-poor aromatic moiety, in contradicto the selective transfer of the sterically less hindered or electron-poor aromatic moiety, in tive transfer of the sterically less hindered or electron-poor aromatic moiety, in contradiction with the previously reported ortho-effect [63]. The free of plausible transition states intermediates is in agreement with the observed selectivity. Base-mediated C-H arylation of α-free BODIPYs for the synthesis of α-arylBODIPY dyes.
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