One-Pot, Two-Step Direct Conversion of Alkenes to Amines Through Tandem Ozonolysis and Ammonia-Borane in Water

Abstract

An efficient, one-pot, two-step reductive amination of alkenes through tandem ozonolysis using ammonia-borane as a reducing agent is described. The reaction has been carried out in water. This is a highly efficient and mild procedure that is applicable to a wide variety of amine substrates. In particular, this is the first successful manifestation that this type of reaction can be carried out in water with ammonia-borane.

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GRAPHICAL ABSTRACT

Keywords:

• Alkenes
• amines
• ammonia-borane; ozone
• water

ACKNOWLEDGMENTS

Vipin Tyagi is thankful to Ch. Charan Singh University, Meerut (Uttar Pradesh), India, for providing necessary research facilities. We are grateful to the Sophisticated Analytical Instrumentation Facility (SAIF), Panjab University, Chandigargh, India, especially Avatar Singh, for providing analytical and spectral data.

Notes

^a No product formation was obtained in polyethylene glycol and toluene.

^b Reductive amination reaction with highly water-soluble amines does not proceed satisfactorily.

^c Yield of isolated product.