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Published June 5, 2025 | Version Supplemental material
Journal Article Open

Direct, Convergent α-Amidation of β-Keto Esters via Nickelocene Catalysis

Creators

  • 1. ROR icon California Institute of Technology

Abstract

α-Amidation of carbonyl-containing compounds without prefunctionalization of starting materials represents a continuing challenge within the scientific community. Here, nickelocene is used catalytically to effect an amidation of β-keto esters. Broad substrate tolerance on both coupling partners is achieved, enabling the application toward a convergent synthetic strategy. Initial mechanistic investigations suggest complex activation pathways.

Copyright and License

© 2025 American Chemical Society.

Supplemental Material

  • Experimental procedures and spectroscopic data (PDF)

Acknowledgement

The National Institutes of Health (NIH)–National Institute of General Medical Sciences (NIGMS) (R35GM145239), Heritage Medical Research Investigators Program, and Caltech are thanked for the support of our research program. The authors also thank Dr. David VanderVelde (Caltech) for his NMR expertise, Dr. Scott C. Virgil (Caltech) for his instrumentation support, and Jay Barbor (Caltech) for helpful discussions. Kimberly R. Sharp and Sara Y. Siddiqui thank the National Science Foundation (NSF) Graduate Research Fellowship Program (GRFP) for funding.

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Additional details

Funding

National Science Foundation Graduate Research Fellowship Program
National Institute of General Medical Sciences
R35GM145239
Heritage Medical Research Investigators Program

Dates

Available
2025-06-05
In press

Caltech Custom Metadata

Caltech groups
Division of Chemistry and Chemical Engineering (CCE)
Publication Status
In Press