Bismuth(III)-catalysed hydroalkylation of styrene with acetylacetone: a DFT-Based mechanistic study

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• An internal hydrogen bond is identified in complex 33 with a distance of 1.604 Å between the OH enol ligand and an OTf ligand. However, this interaction is not strong enough to prevent the proton transfer to styrene via TS33-26 with ΔG‡ 22.3 kcal/mol (Figure 6c). We can also rule out the reaction proceeding from 33 via an internal proton transfer to an OTf ligand followed by the release of HOTf for two reasons. Firstly, it has been shown experimentally that HOTf does not catalyse the reaction (ref. 5). Secondly, a recent computational study of a related bismuth reaction shows that this possibility is a highly endergonic process (ref. 10).
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