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Manuscript File Ketone Synthesis ChemRxiv.pdf (615.92 kB)

Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters

preprint
submitted on 21.04.2019, 05:02 and posted on 23.04.2019, 16:36 by Jiang Wang, Brian P. Cary, Peyton Beyer, Samuel H. Gellman, Daniel Weix
A new strategy for the synthesis of ketones is presented based upon the decarboxylative coupling of N-hydroxyphthalimide (NHP) esters with S-2-pyridyl thioesters. The reactions are selective for the cross-coupled product because NHP esters act as radical donors and the thioesters act as acyl donors. The reaction conditions are general and mild, with over 40 examples presented, including larger fragments and the 20-mer peptide Exendin(9-39) on solid support.

Funding

Mechanistically Guided Cross-Electrophile Coupling Approaches to Useful Csp2-Csp2 and Csp2- Csp3 Bonds

National Institute of General Medical Sciences

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Backbone-modified agonists of B-family GPCRs

National Institute of General Medical Sciences

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Graduate Research Fellowship Program (GRFP)

Directorate for Education & Human Resources

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Biotechnology Training Program

National Institute of General Medical Sciences

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History

Email Address of Submitting Author

dweix@wisc.edu

Institution

University of Wisconsin

Country

United States of America

ORCID For Submitting Author

0000-0002-9552-3378

Declaration of Conflict of Interest

No conflict of interest.

Version Notes

Version 1.

Exports