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Just played around with this. First thing I recognized is that it doesn‘t matter what kind of conversion is done. Paragraph to heading also leads to non-working lists.
I think there is an event handler inside the flipper component which stops propagation of the keys that are registered in the component.
After further investigating this issue, turns out there is a logic in src/components/modules/toolbar/inline.ts where the order should be the other way around:
To reproduce:
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