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Nickel-Catalyzed Barton Decarboxylation and Giese Reactions

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Date

2017-01-02

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Abstract

Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N-hydroxyphthalimide (NHPI) based redox-active esters were found to be convenient starting materials for simple, thermal, Ni-catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH3) or an electron-deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.

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Keywords

conjugate addition, decarboxylation, esters, nickel catalysis, redox-active

Citation

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https://dspace-test.anu.edu.au/handle/1885/733754496

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DevOps Pure Testing

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Angewandte Chemie - International Edition

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DOI

10.1002/anie.201609662

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