Until very recently, most catalytic systems described in the field of C-H activation require forced reaction conditions and carefully designed directing groups. Furthermore, hetereogeneous systems are far less developed than their homogeneous counterparts.<sup> </sup>Herein we present an Ir-based catalyst that performs C-H halogenations at room temperature, using low catalyst loadings. This catalyst allows for the introduction of halogens with a diverse set of directing groups, inherently present in many drug like molecules. In addition, a directed heterogeneous C-H activation/halogenation reaction catalyzed by readily synthesized Pd@MOF nanocatalysts is described. Very high conversions and selectivities were achieved under mild reaction conditions and in short reaction times. A wide variety of directing groups, halogen sources, and substitution patterns were well tolerated, and mono- and/or di-halogenated compounds were synthesized in a controlled manner. Finally, examples of late stage functionalization of advanced druglike molecules will be showcased.

Development of heterogeneous and homogeneous catalysts for directed C-H halogenation reactions: Implications in late stage functionalization

253rd National Meeting (2017)

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