Green Light Promoted Iridium(III)/Copper(I)‐Catalyzed Addition of Alkynes to Aziridinoquinoxalines Through the Intermediacy of Azomethine Ylides

Author:

Zhelavskyi Oleksii1,Parikh Seren1,Jhang Yin‐Jia1,Staples Richard J.2ORCID,Zimmerman Paul M.1ORCID,Nagorny Pavel1ORCID

Affiliation:

1. Chemistry Department University of Michigan Ann Arbor MI 48109 USA

2. Department of Chemistry and Chemical Biology Michigan State University East Lansing MI 48824 USA

Abstract

AbstractThis 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.

Funder

National Institute of General Medical Sciences

Publisher

Wiley

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