Purdue University Graduate School
Development of Amine-Boranes And Derivatives For Reductive Amination.pdf (9.72 MB)
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Development of Amine-Boranes And Derivatives For Reductive Amination.pdf

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posted on 2023-03-10, 13:29 authored by Shivani ChoudharyShivani Choudhary

This dissertation focuses on the development of amine-boranes and their novel monotrifluoroacetoxy-derivatives as efficient and environmentally friendly reagents for reductive amination. Trimethyl borate, as a lewis acid, is shown to improve the chemoselectivity of amine-boranes while promoting faster imine formation. Refinement of amine-boranes via reaction with trifluoroacetic acid provides mono trifluoroacetoxyborane-amine (TFAB-amine) complexes. This new class of reagents serves as mild, chemoselective agents for the direct reductive amination of aldehydes and ketones. Among these, TFAB-NEt3 is established as superior, compared to widely-used reductive amination reagents, with improved yields even for challenging substrates. The application of the monotrifluoroacetoxy-derivatives has been extended for the synthesis of lactams from keto-acids and amino-acids via a tandem reductive amination amidation protocol.


Degree Type

  • Doctor of Philosophy


  • Chemistry

Campus location

  • West Lafayette

Advisor/Supervisor/Committee Chair

P.V. Ramachandran

Additional Committee Member 2

Chittaranjan Das

Additional Committee Member 3

Abram J. Axelrod

Additional Committee Member 4

Hilkka I. Kenttamaa

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