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Rhodium complexes catalyze oxidative coupling between salicylaldehyde and phenylacetylene via C–H bond activation

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A coupling reaction between salicylaldehyde and phenylacetylene was catalyzed by well-defined rhodium complexes, Rh(cod)(l-amino acid) (cod is 1,5-cyclooctadiene; l-amino acid is l-proline, l-phenylalanine and l-valine), to give a flavonoid in 40–88% yield, providing a method for flavonoid synthesis. The coupling reactions catalyzed by Rh(cod)(l-amino acid)s gave higher yields than those by [Rh(cod)Cl]2 without l-amino acid ligands. The reaction mechanism may be that l-amino acid ligands of the rhodium complexes can provide an empty track for phenylacetylene to form a ring structure that fractures to produce the aim flavonoid and RhIX species. Then, the active RhIX specie is oxidized to regenerate RhIIIX3 by Cu(OAC)2.

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This work was supported by the National Natural Science Foundation of China (U1162123) and (51103076), the Natural Science Foundation of Heilongjiang Province of China (LC2011C12), the Overseas Scholars Foundation of the Education Department of Heilongjiang Province of China (1251H012) and the New Century Excellent Talents of the Education Department of Heilongjiang Province of China (1253-NCET-24).

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Correspondence to Hongge Jia, Yanan Tang or Liqun Ma.

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Jia, H., Tang, Y., Shi, Y. et al. Rhodium complexes catalyze oxidative coupling between salicylaldehyde and phenylacetylene via C–H bond activation. Chem. Pap. 71, 1791–1795 (2017).

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