Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Pyridine-4-thiol, is researched, Molecular C5H5NS, CAS is 4556-23-4, about Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions.Electric Literature of C5H5NS.
Heteroaromatic sulfinates, e.g., I, are effective nucleophilic reagents in Pd(0)-catalyzed cross-coupling reactions with aryl halides e.g., 4-methoxy-bromobenzene. However, metal sulfinate salts can be challenging to purify and solubilize in reaction media, and are not tolerant to multi-step transformations. Here base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones were introduced. It was shown that, under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls, e.g., II. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.
This literature about this compound(4556-23-4)Electric Literature of C5H5NShas given us a lot of inspiration, and I hope that the research on this compound(Pyridine-4-thiol) can be further advanced. Maybe we can get more compounds in a similar way.
Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts