53669-32-2Relevant academic research and scientific papers
NHC-Organocatalyzed CAr?O Bond Cleavage: Mild Access to 2-Hydroxybenzophenones
Janssen-Müller, Daniel,Singha, Santanu,Lied, Fabian,Gottschalk, Karin,Glorius, Frank
, p. 6276 - 6279 (2017/05/19)
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.
