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- Title
Green Light Promoted Iridium(III)/Copper(I)‐Catalyzed Addition of Alkynes to Aziridinoquinoxalines Through the Intermediacy of Azomethine Ylides.
- Authors
Zhelavskyi, Oleksii; Parikh, Seren; Jhang, Yin‐Jia; Staples, Richard J.; Zimmerman, Paul M.; Nagorny, Pavel
- Abstract
This manuscript describes the development of alkyne addition to the aziridine moiety of aziridinoquinoxalines using dual Ir(III)/Cu(I) catalytic system under green light‐emitting diode (LED) photolysis (λmax=525 nm). This mild method features high levels of chemo‐ and regioselectivity and was used to generate 30 highly functionalized substituted dihydroquinoxalines in 36–98 % yield. This transformation was also carried asymmetrically using phthalazinamine‐based chiral ligand to provide 9 chiral addition products in 96 : 4 to 86 : 14 e.r. The experimental and quantum chemical explorations of this reaction suggest a mechanism that involves Ir(III)‐catalyzed triplet energy transfer followed by a ring‐opening reaction ultimately leading to the formation of azomethine ylide intermediates. These azomethine intermediates undergo sequential protonation/copper(I) acetylide addition to provide the products.
- Subjects
YLIDES; RING-opening reactions; IRIDIUM; COPPER; CHEMICAL reactions; ALKYNES
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 12, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202318876