One of the key advantages of the direct C-H functionalization approach is the absence of pre-activation steps. Thus, molecular complexity can be achieved in a single chemical step. A large disadvantage however, aside from the C-H regio-selectivity issue, resides in the often necessary pre-activation or pre-oxidation of the coupling partner such that it becomes sufficiently reactive for the coupling reaction to occur. In contrast, the concept of cross dehydrogenative coupling is appealing because it typically avoids any pre-activation or pre-oxidation of either coupling partners. Nevertheless, the latter concept usually relies on an externally applied oxidizing principle, often harshening reaction conditions, limiting chemo-selectivity, functional group tolerance, or even the overall atom efficiency of the process. In this lecture, I will discuss our efforts at developing novel oxidizing strategies for the design of efficient synthetic methods.
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