These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
photochemical alpha alkylation of amines.pdf (1.38 MB)
Photocatalytic α-Alkylation of Amines with Alkyl Halides
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 28.09.2020 and posted on 29.09.2020by Lingying Leng, Joseph Ready
a-Branched amines represent essential building
blocks for organic synthesis. They are traditionally prepared through
nucleophilic addition to imines. These methods often require highly reactive
organometallic reagents and proceed under rigorous air- and moisture-free
conditions. Here we describe an alternative approach that involves a net
dehydrogenative coupling between alkyl bromides and amines. Mechanistically,
the reaction likely involves photocatalytic generation of an a-amino
radical and a stabilized carbon-centered radical (allyl, benzyl, a-carbonyl)
followed by radical recombination. This approach offers a mild,
atom-economical, redox neutral synthesis of a-branched amines that
shows broad scope and avoids pre-metalated reagents.