One‐Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)‐Catalyzed Multiple CH Activation and Annulation

Abstract

A new method for the synthesis of highly substituted naphthyridine-based polyheteroaromatic compounds in high yields proceeds through rhodium(III)-catalyzed multiple C-H bond cleavage and C-C and C-N bond formation in a one-pot process. Such highly substituted polyheteroaromatic compounds have attracted much attention because of their unique π-conjugation, which make them suitable materials for organic semiconductors and luminescent materials. Furthermore, a possible mechanism, which involves multiple chelation-assisted ortho C-H activation, alkyne insertion, and reductive elimination, is proposed for this transformation.

Transition Metal‐Catalyzed Reactions Involving Oximes

“…In 2014, Chuang and Cheng et al. realized a rhodium(III)‐catalyzed multiple C–H activation and annulation of N ‐hydroxybenzamidines (benzamidoxime) with symmetrical alkynes, delivering naphthyridine‐based polyheteroaromatic compounds in one pot (Scheme ) . Reactions of benzamidines bearing electron‐poor or electron‐rich groups could take place with both aromatic and aliphatic alkynes very well, affording the desired products in good yields (Scheme ).…”

Palladium‐Catalyzed Selective Aryl Ring C–H Activation of N‐Acyl‐2‐aminobiaryls: Efficient Access to Multiaryl‐Substituted Naphthalenes

“…[3] Therefore, direct ring construction through the use of metal-catalyzed multiple CÀH bond functionalizations with internal alkynes as an inserting unit has provided an opportunity for the synthesis of bioactive or polyaromatic pconjugated molecules. [5] Wu and coworkers developed an Nacyl-directed consecutive CÀH bond activation and insertion of alkynes on anilides, leading to tetraarylsubstituted naphthalenes (Scheme 1a). [5] Wu and coworkers developed an Nacyl-directed consecutive CÀH bond activation and insertion of alkynes on anilides, leading to tetraarylsubstituted naphthalenes (Scheme 1a).…”

Rh‐Catalyzed Synthesis of Nitrogen‐Containing Heterocycles

“…(5.78)) [42]. This interesting new chemistry delivers highly substituted -conjugated compounds, which can potentially be used in organic semiconductors and luminescent materials.…”