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- Title
1,10‐Phenanthroline Copper(I) Complexes with A<sup>3</sup> Coupling to Access Allenes for Cycloaddition Reactions.
- Authors
Kim, Hyun Jo; Lee, Ji Eun; Koyyada, Ganesh; Lakavathu, Mohan; Kim, Jae Hong
- Abstract
Propargylamines are significant building blocks for the generation of polyfunctional amino analogues, natural products, and pharmacologically active drugs. Herein we report the most straightforward approach is to use 1,10‐phenanthroline copper(I) complexes as a catalyst to promote the (Alkyne‐Alkyne‐Amine) A3 coupling reaction between cyclic secondary amines and two terminal alkynes that generates a ketimine intermediate in situ through hydroamination, which subsequently interacts with the alkenyl copper complex to produce tetrasubstituted propargylamine. In the addition of zinc halide, the propargylamines converted into trisubstituted allenes with up to 90% yield. When Sc(OTf)3 is used to perform the [4+2] cycloaddition reaction with enophile (alkene), the cyclized product obtained in up to 72% yield. On the other hand, the allene was subjected to a metal‐free intermolecular cyclization reaction to produce the highly substituted pyridine derivative, although this provides only up to 30% yield.
- Subjects
RING formation (Chemistry); ALLENE; ZINC halides; COPPER; ALKENES; CATALYSTS; COPPER compounds; PROPARGYLAMINES
- Publication
Asian Journal of Organic Chemistry, 2022, Vol 11, Issue 4, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202200053