Highly efficient and recyclable water-soluble fullerene-supported PdCl₂ nanocatalyst in Suzuki–Miyaura cross-coupling reaction

Abstract

A water-soluble fullerene-supported PdCl 2 nanocatalyst [C 60 -TEG S /PdCl 2 ] was prepared by coordination of water-soluble fullerene nanoparticles with palladium chloride. In pure water, the catalytic activity of nanocatalyst [C 60 -TEG S /PdCl 2 ] for Suzuki-Miyaura cross-coupling reaction was investigated under different reaction conditions. The results showed that biphenyl compounds could be synthesized in high yields at room temperature using 0.01 mol% of [C 60 -TEG S /PdCl 2 ] as the catalyst and K 2 CO 3 as the base with the reaction time of 4 h. The catalyst was recycled five times, and the yield clearly did not decrease.

About Solid Phase vs. Liquid Phase in Suzuki-Miyaura Reaction

“…Veisi et al [70] used a Pd supported on NPs of magnetic iron (Fe 3 O 4 ), in 7 successive runs with 4-bromoanisole. Only 5% of Pd was leached at the last run giving a homogeneous activity 20 times more then the heterogeneous one and the same results were obtained with 4-bromoacetophenone [73] giving a TOF leach one order of magnitude higher than TOF tot (Entry 4, Table 3).…”

“…Another example comes from the work of Chtchigrovsky et al [93] who used 0.0001 mol% of Pd, which represents only 10 ppb of Pd. Other examples, even at ppm levels are also ambiguous (e.g., [73,91], . .…”

Green synthesis of biphenyl carboxylic acids via Suzuki–Miyaura cross-coupling catalyzed by a water-soluble fullerene-supported PdCl2 nanocatalyst

“…[5][6][7][8] Recently we synthesized a fullerene-supported PdCl 2 nanocatalyst (Figure 1) and successfully used it to synthesize biphenyl compounds via a Suzuki-Miyaura cross-coupling of aryl bromides and chlorides with aryl boronic acids. 9 We now report its successful use in synthesizing biphenyl carboxylic compounds via a Suzuki-Miyaura cross-coupling of aryl bromides containing a carboxyl group with aryl boronic acids.…”