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Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents

preprint
submitted on 08.09.2020 and posted on 09.09.2020 by Preeti P. Chandrachud, Lukasz Wojtas, Justin Lopchuk

The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C–N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.

Funding

NSF (CHE-1903144)

ACS PRF (59537-DNI1)

NIH NCI (P30-CA076292)

History

Email Address of Submitting Author

justin.lopchuk@moffitt.org

Institution

H. Lee Moffitt Cancer Center & Research Institute

Country

USA

ORCID For Submitting Author

0000-0002-6910-6132

Declaration of Conflict of Interest

None

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