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An unprecedented Rh(III)-catalyzed cascade C-H activation/Lossen rearrangement of aromatic amides with methyleneoxetanones has been realized along with a tunable C-N bond reductive elimination/trans esterification, giving divergent access to quinolinones and… Click to show full abstract
An unprecedented Rh(III)-catalyzed cascade C-H activation/Lossen rearrangement of aromatic amides with methyleneoxetanones has been realized along with a tunable C-N bond reductive elimination/trans esterification, giving divergent access to quinolinones and dihydroisoquinolinones via selective ring-opening of the four-membered lactone unit. Combined computational and experimental mechanistic studies defined the solvent-involved distinguished reaction paths, the origin of the observed chemodivergence, as well as the role of the substituent attached at the oxidizing directing group in tuning the reaction outcomes.
Journal Title: Organic letters
Year Published: 2020
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