While (cyclopentadienone)iron carbonyl compounds have been known since the late 1950s, their use as catalysts in transfer hydrogenations and dehydrogenations has only been explored during the last decade. These air-stable compounds, which resemble Shvo’s diruthenium bridging hydride in both structure and function, catalyze alcohol oxidations, carbonyl reductions, borrowing hydrogen transformations, and cycloisomerizations of allenes. A rational extension of these applications is to the oxidative lactonization of diols, but only a few examples of this transformation have been shown with this class of iron compounds. We have explored the reactivity of a range of (cyclopentadienone)iron tricarbonyl compounds in the oxidative lactonization of both symmetrical and unsymmetrical diols. Our results illustrate that lactone yield is highly dependent on the structure of the cyclopentadienone ligand, especially when unsymmetrical diols are used. When the appropriate catalyst is chosen, high conversions of diols into 5-, 6-, and 7-membered lactones can be achieved.

(Cyclopentadienone)iron-catalyzed lactonizations of symmetrical and unsymmetrical diols

2019 Spring National Meeting

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