Enantio- and regioselective nickel/photoredox-catalyzed cross-electrophile coupling of benzylic aziridines with alkynyl bromides.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 42102202.
- Also identified by DOI 10.1126/sciadv.aef4526 and PMC identifier 13155299.
- Licence recorded as CC BY-NC.
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Abstract
Alkynes with a proximal stereogenic center are a key structural element of many bioactive compounds, chemical probes, and functional materials and serve as a valuable synthon in organic synthesis. Here, a nickel/photoredox-catalyzed asymmetric C(sp<sup>3</sup>)─C(sp) cross-electrophile coupling (XEC) between racemic aryl aziridines and readily available alkynyl bromides was achieved in an enantioconvergent manner, affording β-alkynylethylamines in good to excellent enantioselectivity with complete regiocontrol. The obtained enantioenriched benzylic alkynes are indeed versatile synthetic intermediates and can be readily transformed into various synthetically useful chiral synthons and biologically active molecules, such as valuable β-ethylamine derivatives, heterocyclic amines, and β<sup>2</sup>-amino acids. Mechanistic studies were indicative of the aziridine being activated through a regioselective nucleophilic halide ring opening and subsequent enantioselective XEC of the generated β-amino benzyl halides with alkynyl bromides.