Ruthenium Catalyst in Coupling Reaction of Alcohols with Primary Amines

Chloro(p-cymene)[2-[(di-tert-butylphosphino)methyl]pyridine]ruthenium(II) triflate (1) catalyzes the reaction of benzyl alcohol derivatives with primary amines to yield secondary amines.¹⁾ The advantage of this reaction is it does not require any additives or solvents. Apparently, chemoselective dehydration condensation of benzyl alcohol derivatives with primary amines can proceeds even in the presence of unprotected phenols or anilines. In addition, it has been reported that the tandem Pictet-Spengler reaction of alcohols and N-benzyltryptamines affords tetrahydro-β-carbolines in presence of 1 and a Lewis acid catalyst like In(OTf)₃.²⁾

Related Product

C3668

Chloro(p-cymene)[2-[(di-tert-butylphosphino)methyl]pyridine]ruthenium(II) triflate

References

• 1) A Base and Solvent-Free Ruthenium-Catalyzed Alkylation of Amines
  • J. J. A. Celaje, X. Zhang, F. Zhang, L. Kam, J. R. Herron, T. J. Williams, ACS Catal. 2017, 7, 1136.
• 2) Ruthenium Catalyzed Tandem Pictet–Spengler Reaction
  • A. Nalikezhathu, V. Cherepakhin, T. J. Williams, Org. Lett. 2020, 2, 4979.