Scheme for introduction of secondary alkyl groups at the meta-position using cat. C3456 and K2CO3 [P1748] in dioxane at 100 °C, with pyridine as directing group.

Ruthenium Catalyst for C-H Activation at the meta-Position of a Directing Group

(p-Cymene)bis(mesitylcarboxylato)ruthenium(II) [C3456] is a ruthenium catalyst used for C-H bond functionalization. It enables meta-selective C-H functionalization of substituted benzene rings, allowing secondary alkyl groups to be introduced at the meta-position, for example with secondary alkyl halides. The catalyst is also applicable for ortho-selective decarboxylative C-H functionalization of benzoic acid derivatives. In the case of o-alkylbenzoic acid derivatives treated with alkenes, it provides meta-alkenylated arenes. In the meta-alkylation scheme, Potassium Carbonate (P1748) is used as the base in dioxane at 100 °C. These reactions were reported by Hofmann and Ackermann¹) and by Kumar, Ackermann et al.²)

Scheme for introduction of secondary alkyl groups at the meta-position using cat. C3456 and K2CO3 [P1748] in dioxane at 100 °C, with pyridine as directing group.
Source: TCI brochure RR123
Scheme for decarboxylative C-H functionalization of a benzoic acid derivative with methyl acrylate using cat. C3456 and V2O5 in toluene at 100-120 °C.
Source: TCI brochure RR123

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References

  1. meta-Selective C–H Bond Alkylation with Secondary Alkyl Halides. N. Hofmann, L. Ackermann, J. Am. Chem. Soc. 2013, 135, 5877. doi:10.1021/ja401466y
  2. Ruthenium(II)‐Catalyzed Decarboxylative C−H Activation: Versatile Routes to meta‐Alkenylated Arenes. N. Y. P. Kumar, L. Ackermann, et al., Angew. Chem. Int. Ed. 2016, 55, 6929. doi:10.1002/anie.201600490

Download TCI brochure Ruthenium Catalyst for the C-H Activation at meta-Position of Directing Group (PDF)

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