Abstract
PdCl2 immobilized in polyacrylamide (PAM), named Pd/PAM, produced at an extremely low cost, was found to be an efficient catalyst for Suzuki-Miyaura cross-coupling reactions. Iodo- and bromoarenes may couple with phenylboronic acid under eco-friendly conditions (i.e., phosphine-free and with ethanol as the solvent) to give excellent product yields. Aryl chlorides, in contrast, were found to be unsuitable reagents in this context, yielding modest results. The recyclability of Pd/PAM is limited because of PdII leaching, which leaves only the base polymer on the surface after six runs. The Pd/PAM catalyst was initially prepared via the formation of a PAM hydrogel using an aqueous PdCl2 solution. After drying, the solid Pd/PAM was characterized by scanning electron microscopy (SEM), electron-dispersive spectroscopy (EDS), Fourier transform infrared spectroscopy (FTIR), and inductively coupled plasma optical emission spectrometry (ICP OES).
Highlights
Suzuki-Miyaura cross-coupling is a versatile reaction in organic chemistry that is typically catalyzed by palladium salts with auxiliary ligands.[1]
The catalytic properties of Pd/PAM were evaluated for the Suzuki-Miyaura cross-coupling of 4-iodoanisole with phenylboronic acid (Scheme 1)
When the same reaction was repeated without PAM but with the same PdCl2 load, the yield decreased to 23%
Summary
Suzuki-Miyaura cross-coupling is a versatile reaction in organic chemistry that is typically catalyzed by palladium salts with auxiliary ligands.[1]. A Schlenk reactor was charged with base (2 mmol), phenylboronic acid (187 mg, 1.5 mmol), aryl halide (1 mmol), Pd/PAM catalyst (120 mg, 0.3 mol% of Pd), undecane (internal standard, 10 μL), and solvent (3 mL). The polymeric solid Pd/PAM was characterized, and its catalytic properties in Suzuki‐Miyaura cross-coupling reactions were investigated.
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