Synlett 2019; 30(18): 2022-2026
DOI: 10.1055/s-0037-1611911
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© Georg Thieme Verlag Stuttgart · New York

Regioselective Radical Alkene Amination Strategies by Using Phosphite-Mediated Deoxygenation

Samuel W. Lardy
,
Valerie A. Schmidt
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093, USA   Email: vschmidt@ucsd.edu
› Author Affiliations
This work was supported by start-up funds provided by the University of California, San Diego.
Further Information

Publication History

Received: 08 July 2019

Accepted after revision: 30 July 2019

Publication Date:
09 August 2019 (online)

Abstract

Nitrogen-containing compounds are an essential motif in all disciplines of chemistry and the efficient synthesis of these frameworks is a highly sought-after goal. Presented here is a summary of recent efforts conducted by our group to develop radical-mediated amination strategies for the formal synthesis of primary amines from alkenes with exclusive anti-Markovnikov regioselectivity. We have found that N-hydroxyphthalimide is an effective reagent capable of supplying both the N and H atoms for alkene hydroamination in a group transfer radical addition-type mechanism. Furthermore, allyl-oxyphthalimide derivatives are similarly capable of radical group transfers and allow for the aminoallylation of an external alkene.

 
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