Palladium‐catalyzed Heck coupling of 2‐vinylpyridine with aryl chlorides

Abstract

An efficient PdCl 2 (PCy 3 ) 2 -catalyzed cross-coupling reaction of 2-vinylpyridine with aryl chlorides to afford trans-2-styrylpyridines with a variety of functional groups on the benzene ring is described.

Convenient Access to Acyl‐Substituted Bis(styrylbenzenes) Based on Building Blocks Using Julia Olefination and Weinreb Amide Chemistry

“…The compounds 13, [11] 14a, [12] 30, [19] 31, [20] 32, [21] and 36 [22] are known in the literature.…”

Base-Promoted SNAr Reactions of Fluoro- and Chloroarenes as a Route to N-Aryl Indoles and Carbazoles

“…Recently, we have also developed the application of KOH/DMSO in the synthesis of five-membered heterocycles via the cycloaddition of 1,3-butadiynes with H 2 O, primary amines, Na 2 S·9H 2 O [25], and in nucleophilic fluoroarene substitutions with a variety of nucleophiles to provide an alternative base-promoted S N Ar of C−F bonds [26]. In continuation of our interest in the development of highly atom-economic reactions through C-Cl bond activation in aryl chlorides and their transformation [27,28,29,30,31,32], we have investigated the N -arylation of indoles and carbazole by the nucleophilic aromatic substitution ( S N Ar ) protocol from chloroarenes and fluoroarenes in the presence of KOH in DMSO. The N -arylation of indoles and carbazoles through transition- metal-catalyzed catalysis have been well studied [33,34,35,36,37,38], and a microwave-assisted N -arylation of indoles via S N Ar in the presence of K 2 CO 3 or Cs 2 CO 3 under microwave irradiation in DMSO [39], KO t Bu-promoted N -arylations of carbazoles using diaryliodonium salts [40] have also been reported.…”

Comparative Study of the Frech Catalyst with Two Conventional Catalysts in the Heck Synthesis of 2,4-Diaminopyrimidine-based Antibiotics

“…8,10 Conventional catalysts also give modest results with heterocyclic substrates. 11,12 In contrast, the Frech catalyst exhibits robust thermal stability due, in large part, to the P-Pd-P (PCP) moiety of the pincer ligand. 5,13 This thermal stability, together with its inertness to oxygen and water, are unique qualities of the Frech catalyst and allow it to maintain high activity under a variety of reaction conditions.…”