Synthesis of Fused Lactones through Transition‐Metal‐Catalyzed peri C−H Functionalization

Abstract

The rhodium(III)‐catalyzed dehydrogenative cyclization of 9‐anthracenecarboxylic acids and 2‐substituted 1‐naphthoic acids proceeds through peri C−H bond cleavages to produce fused lactones. These aromatic carboxylic acids also undergo dehydrogenative coupling with styrenes and successive Wacker‐type cyclization under palladium catalysis to construct 3‐benzylidenebenzo[de]isochromen‐1‐one frameworks.

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part C: The Domino Diarylation and Annelation Reactions

“…According to computational calculations [70] Recently, Satoh and co-workers related the synthesis in a low yield of fused six-membered lactone 19 g1 from dehydrogenative coupling of 9-anthracenecarboxylic acid 19 g with styrene using Pd-(OAc) 2 as the catalyst and AgOAc as the oxidant (Scheme 19g). [71] The process was greatly improved with KOAc additive but, as pointed out by the authors, its role remains obscure. The catalytic cycle depicted in Scheme 19h somewhat differs from the one published.…”