Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands and Their Applications in Cu-Mediated N-H Insertion Reaction

Daniel M Knoll; Yuling Hu; Zahid Hassan; Martin Nieger; Stefan Bräse

doi:10.3390/molecules24224122

Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands and Their Applications in Cu-Mediated N-H Insertion Reaction

Molecules. 2019 Nov 14;24(22):4122. doi: 10.3390/molecules24224122.

Authors

Daniel M Knoll¹, Yuling Hu¹, Zahid Hassan¹, Martin Nieger², Stefan Bräse^{1

3}

Affiliations

¹ Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
² Department of Chemistry, University of Helsinki, P.O. Box 55 A.I. Virtasen aukio 1, 00014 Helsinki, Finland.
³ Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, D-76344 Eggenstein-Leopoldshafen, Germany.

Abstract

New catalysts for important C-N bond formation are highly sought after. In this work, we demonstrate the synthesis and viability of a new class of planar chiral [2.2]paracyclophane-based bisoxazoline (BOX) ligands for the copper-catalyzed N-H insertion of α-diazocarbonyls into anilines. The reaction features a wide substrate scope and moderate to excellent yields, and delivers the valuable products at ambient conditions.

Keywords: N–H insertion; [2.2]paracyclophane ligands; copper catalysis; planar chirality; α-diazocarbonyls.

MeSH terms

Catalysis
Copper / chemistry*
Ligands
Molecular Structure
Polycyclic Compounds / chemistry*
Stereoisomerism

Substances

Ligands
Polycyclic Compounds
Copper

Grants and funding

TR88/3MET/SFB