Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

NHC-Organocatalyzed CAr−O Bond Cleavage: Mild Access to 2-Hydroxybenzophenones

NHC-Organocatalyzed CAr−O Bond Cleavage: Mild Access to 2-Hydroxybenzophenones
Santanu Singha, Karin Gottschalk, Frank Glorius, Fabian Lied, Daniel Janssen-Müller
A Truce–Smiles rearrangement of acyl-anion equivalents generated by N-heterocyclic carbene (NHC) catalysis has been achieved. The developed method includes CAr−O, CAr−S, or CAr−N bond cleavage for the formation of a CAr−C bond and enables access to 2-hydroxybenzophenones, an important structural motif that is present in several bioactive natural products. By utilizing this procedure, the alkaloid taxilamine was synthesized in three steps. DFT calculations and control experiments support a classical SNAr mechanism with a catalyst-bound Meisenheimer-type intermediate. The method features mild reaction conditions, excellent functional-group tolerance, and a broad substrate scope, including various classes of (hetero)arenes. Catalysis with Smiles: A Truce–Smiles rearrangement of acyl-anion equivalents generated by N-heterocyclic carbene (NHC) catalysis has been achieved. The developed method includes CAr−O, CAr−S, or CAr−N bond cleavage for the formation of a CAr−C bond and enables access to 2-hydroxybenzophenones, an important structural motif present in several bioactive natural products.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201610203

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