Directing groups play an important role in controlling the selectivity of C–H bond activation. Here we demonstrate that for iron, the nature of the directing group (e.g., ketone, ester, or amide) has large consequences for the C–H activation process. In particular,we show that C–H bond activation either occurs with or without assistance of the directing group resulting in distinct cis- and trans-isomers of the corresponding iron hydride. Computational studies were used to shed more light on this directing group based divergence, which is further discussed in this report

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