"Click" chemistry with CuAIAC


Since its definition by Sharpless and co-workers in 2001, “click” chemistry has become an important methodology of modern synthetic organic chemistry. Within a variety of “click” reactions, the Cu-catalyzed azide−alkyne cycloaddition (CuAAC), discovered independently by the groups of Meldal and Fokin and Sharpless, has been the first and the most prominent example of the “click” reaction. Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) has been published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Following the seminal paper of Fu (JACS 2003, JACS 2005) and Pale and Sommer (CEJ 2009), we have been the third group to report CuAIAC reactions (AJC 2009). Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. Reactions between pyrazolidinone-1-azomethine imines and terminal ynones give yellow fluorescent cycloadducts. The availability of azomethine imines, mild reaction conditions, simple workup, and scalability make CuAIAC a viable supplement to the Cu-catalyzed azide−alkyne cycloaddition reaction in “click” chemistry. In this context, the aim and objectives of our research are the following:

  • To prepare new Cu0- and Cu2+-based catalysts.
  • To study and demonstrate their applicability in CuAIAC.
  • To study the catalytic mechanism of CuAIAC.
  • To develop new methods for determination of absolute configuration of products of CuAIAC.
  • To demonstrate applicability of CuAIAC in fluorescent labelling, bioconjugation, and materials science.
<p>&quot;Click&quot; Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine&minus;Alkyne Cycloadditions</p>

"Click" Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine−Alkyne Cycloadditions

<p>Absolute Configuration Determination of 2,3-Dihydro‑1H,5H‑pyrazolo[1,2‑a]pyrazoles Using Chiroptical Methods at Different Wavelengths</p>

Absolute Configuration Determination of 2,3-Dihydro‑1H,5H‑pyrazolo[1,2‑a]pyrazoles Using Chiroptical Methods at Different Wavelengths

<p>Cu0-catalysed 1,3-dipolar cycloadditions of &alpha;-amino acid derived N,N-cyclic azomethine imines to ynones</p>

Cu0-catalysed 1,3-dipolar cycloadditions of α-amino acid derived N,N-cyclic azomethine imines to ynones

<p>Copper-Catalyzed Azomethine Imine&ndash;Alkyne Cycloadditions (CuAIAC). Review article.</p>

Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC). Review article.

<p>2-Acyl-1-aryl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole derivatives: Versatile fluorescent probes with remarkably large Stokes shift</p>

2-Acyl-1-aryl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole derivatives: Versatile fluorescent probes with remarkably large Stokes shift

<p>Synthesis of 6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles by azomethine imine-alkyne cycloadditions using immobilized Cu(II)-catalysts</p>

Synthesis of 6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles by azomethine imine-alkyne cycloadditions using immobilized Cu(II)-catalysts