Steric effect of substituents in haloarenes on the rate of cross-coupling reactions

Application of palladium complexes bearing acyclic amino(hydrazido)carbene ligands as catalysts for copper-free Sonogashira cross-coupling

“…Thus, palladium complexes with ADC ligands were successfully employed in Suzuki-Miyaura [5][6][7], Heck [3,4,7], Buchwald-Hartwig [3,4], and Sonogashira reactions [3,4,[7][8][9][10][11]. Among them, Sonogashira coupling is typically performed in the presence of a copper co-catalyst (that improves reaction efficiency but brings about the generation of undesired by-products) [12][13][14][15][16][17], although a few copper-free systems, that are free from above disadvantages, are also known.…”

Sterically enhanced 2‐iminopyridylpalladium chlorides as recyclable ppm‐palladium catalyst for Suzuki–Miyaura coupling in aqueous solution

“…As reported in the literature, the SMC of ortho ‐substituted substrates is difficult to obtain due to presence of bulky groups at ortho position, which in result lead to lower yields. [ 19 ] By contrast, this catalytic system gave excellent yield for the coupling reaction of benzeneboronic acid with sterically hindered 2,4,6‐trimethylbromobenzene ( 23 , Scheme 2). Furthermore, the dual coupling of 4‐bromo‐1‐iodobenzene with 1‐naphthalenylboronic acid was also successfully achieved ( 24 , Scheme 2).…”

“…The PerkinElmer System and Flash EA 1112 microanalyzer were employed to measure the FT-IR and elemental analysis data, respectively, whereas 1 H, 13 C, and 19 F NMR data were collected by the Bruker Avance III 400-MHz HD spectrometer at 298 K. The highresolution MS spectra of Pd1-Pd7 were measured on the Bruker Solarix 9.4-T high-resolution FT-MS mass spectrometer. The residual quantity of the palladium was measured by ICP-MS using Agilent ICPMS 7700.…”

The Utility of Sonogashira Coupling Reaction for the Derivatization of Aryl Halides with Fluorescent Alkyne

“…We expect that the formation of diphenyl acetylene by the reaction of DIB-ET with aryl halides should not be hindered in the presence of ortho-substituted functional group compared with the formation of biphenyl by the reaction of DPA and aryl halides. [13][14][15][16] In this work, we firstly evaluated the usefulness of the proposed derivatization technique with DIB-ET for the HPLC analysis of aryl halides using aryl bromides as model analytes. Subsequently, we investigated the reactivity of DIB-ET towards ortho-, meta-and para-substituted aryl bromides; the results were compared with those of the previous derivatization technique that used DPA.…”