Abstract
Abstract This paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation. These reactions were catalyzed by Rh(l-amino acid)(cod) (the l-amino acid is l-phenylalanine, l-valine or l-proline; cod is 1,5-cyclooctadiene) to obtain chromones in 12.7–88.3% yield. These new Rh catalysts have excellent activity for the coupling reaction between phenylacetylene and different benzaldehyde derivatives. It was found that the electronic effects of the benzaldehyde derivative substituent affected the reaction yield, which is in accordance with the proposed mechanism.
Highlights
In previous studies, rhodium catalysts have been used in many different domains, such as oxidative couplingOxidative coupling reactions have been carried out by using Au catalysts [12,13], Fe catalysts [14], Ir catalysts [15,16], Cu catalysts [17,18], Pd catalysts [19,20], and Ru catalysts [21]
This paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation
The Rh catalysts can activate the C-H bond in compounds 1a-1g to react with the triple bond of phenylacetylene, which produces final compounds (3a-3g)
Summary
Rhodium catalysts have been used in many different domains, such as oxidative coupling. One kind of Rh catalyst, which contains Cp* (Cp* = 1,2,3,4,5-Pentamethylcyclopentadiene (C5Me5) ligands, has been used to catalyze oxidative coupling reactions. We synthesized Rh(l-amino acid)(cod)s, which are chiral, highly selective and highly active Rh complexes [11]. In this paper, these Rh complexes were used in oxidative coupling reactions between phenylacetylene and benzaldehyde derivatives. We did not determine the actual mechanism of the Rh-diene complexes, i.e., Rh(l-amino acid)(cod), in oxidative coupling reactions, but we have discussed a possible mechanism in our. The oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives was catalyzed by Rh with an l-amino acid ligand, plus the catalytic efficiencies and substituent electronic effects are discussed
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