In the last 30 years, C–C cross coupling reactions have become a reliable technique in organic synthesis due their versatility and efficiency. While drawbacks have been experienced on an industrial scale with the use of homogenous systems, many attempts have been made to facilitate a heterogeneous renaissance. Thus, this review gives an overview of the current status of the use of heterogeneous catalysts particularly in Suzuki and Heck reactions. Most recent developments focus on palladium immobilised or supported on various classes of supports, thus this review highlights and discuss contributions of the last decade.

The water-soluble ruthenium(II) mononuclear complexes [CpRu(CO) 2 NH 2 R]BF 4 (Cp = η 5 -C 5 H 5 ; R = C 6 H 11 (1), C 6 H 5 (2), CH 2 C 6 H 5 (3), CH(CH 3 )C 6 H 5 (4), CH 2 (C 6 H 4 O)CH 3 (5), CH 2 (C 6 H 4 )CN ( 6), C 6 H 2 (CH 3 ) 3 (7), CH 2 CHCH 2 (8), CH(CH 3 ) 2 ( 9)) were synthesized from the reaction of the organometallic Lewis acid [CpRu(CO) 2 ]BF 4 with amine ligands at room temperature. These complexes are reported for the first time and have been fully characterized by IR, high-resolution mass spectrometry, 1 H and 13 C NMR spectroscopy, and elemental analysis. Spectral data show that the amines are σ-bonded to the metal center via the nitrogen atom. The crystal structures of complexes 3 and 8 were determined by single-crystal X-ray crystallography. The 4-methoxybenzylamine, 4-aminomethylbenzonitrile and allylamine groups preferentially bind to the metal center via the amine nitrogen. The ruthenium complexes 1 , 3 − 6 , 9 , and [CpRu(CO) 2 NH 2 CH 3 ]BF 4 ( 10) and the dinuclear complex [CpRu-(CO) 2 NH 2 (CH 2 ) 6 NH 2 (CO) 2-RuCp][BF 4 ] 2 (11) demonstrated excellent catalytic activity in the oxidation of styrene using NaIO 4 as the co-oxidant with over 95% conversion and benzaldehyde yields, respectively, in some cases.

PdCuCeO was applied for Suzuki–Miyaura coupling in pure water. The catalyst was highly active (TOF > 3000 h−1) and could be reused.

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