A Highly Efficient Catalyst for the Suzuki Cross-coupling Reaction of 3-Chloro-5-oxadiazol-2-yl Pyridine

Abstract

A facile access to diversely substituted 3-aryl/heteroaryl-5-oxadiazol-2-yl-pyridines using PdCl 2 (dtbpf) as palladium precursor has been developed. The method is compatible with a wide range of aryl/heteroaryl boronic acids.J. Heterocyclic Chem., 52, 1748Chem., 52, (2015. a Isolated yields. b Method B: 4 mol% catalyst, Na 2 CO 3 (2.5 equiv.), 3a (1 equiv.) 4a (1.2 equiv.), sealed vial, 90°C, 15 h, 1,4-dioxane/H 2 O.

Application of Palladium Based Precatalytic Systems in the Suzuki‐Miyaura Cross‐Coupling Reactions of Chloro‐ Heterocycles

“…In our successful trials, we have explored an efficient, active and sterically bulky palladium precursor [1,1‐bis(di‐tert‐butylphosphino)ferrocene]palladium(II)dichloride which generates highly active L 2 ‐Pd(0) catalytic species for derivatisation of less reactive 3‐chloro‐5‐oxadiazole‐2‐yl pyridines. The report explains the tolerance of the catalytic system towards wide range of electron rich and electron deficient aryl/heteroaryl boronic acids (Scheme ). A wide range of (hetero)aryl derivatives containing a pyridyl core with an oxadiazol framework were synthesized which can have potential applications in the field of medicinal chemistry.…”

A Highly Efficient Catalyst for the Suzuki‐Miyaura Cross‐Coupling Reaction of 5‐(5‐chloropyridin‐3‐yl)‐3‐methyl‐1,3,4‐oxadiazol‐2(3H)‐one

“…Accordingly, halogenated heterocycles have proven as important synthons in accomplishing this wide range of applications. Owing to the importance of hetero (aryl) fragment in the modern field of medicinal chemistry and as a part of our research on carbon–carbon bond forming reactions of chloro heterocycles , we were interested in the Suzuki‐Miyaura cross‐coupling reactions of 3‐chloro oxadiazolyl pyridine (Fig. ).…”