Aromatic Ring-Opening Metathesis

28 May 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Aromatic compounds have found paramount utility on account of their stability, characteristic interactions, defined molecular shape and the numerous synthetic approaches for their synthesis, which include a diversity of cyclization reactions. In contrast, the cleavage of the inert aromatic carbon-carbon bonds remained largely unfeasible due to the unfavourable energetics of disrupting aromaticity in the formation of ring-opened products. For non- aromatic structures, alkene metathesis catalysed by transition metal alkylidenes is established as one of the most versatile carbon-carbon bond-forming and breaking reactions. However, despite remarkable advancements, strategies to open aromatic compounds by metathesis remained elusive. Herein we disclose the feasibility of aromatic ring-opening metathesis (ArROM) to cleave a diversity of aromatic rings, including tetraphene, naphthalene, indole, benzofuran and phenanthrenes by employing Schrock- Hoveyda molybdenum alkylidene catalysts. The reactions for each of the ring systems thereby proceed through unique alkylidene intermediates. We further show the possibility for stereoselective aromatic ring-opening metathesis with exquisite catalyst control over the configuration of atropisomers. Aromatic ring-opening metathesis is therefore a viable and efficient approach to catalytically transform and interconvert various aromatics without the requirement for any reagents or photoexcitation.




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