6-Diphenylphosphinopyridin-2-(1H)-one (6-DPPon)

Dedicated with best wishes to Prof. Dr. Bernhard Breit at Albert-Ludwigs-Universität Freiburg

Introduction

Among heterocyclic structural units, pyridines are the most prevalent and have attracted the attention of chemists.[1] One important aspect of pyridine chemistry is designing new ligands based on the pyridine core.[2] Inspired by DNA base pairing, 6-DPPon (white solid, mp: 187 °C) was introduced by Bernhard Breit (Albert-Ludwigs-Universität Freiburg) as a monodentate ligand.[3] This compound can not only be easily prepared (Scheme [1]) but also has a brilliant property: the ability for self-assembly.[4]

Scheme 1 Preparation of 6-DPPon

6-DPPon has two tautomeric forms, a 2-pyridone and a 2-hydroxypyridine tautomer (Scheme [2]).

Scheme 2 Tautomeric forms of 6-DPPon

Interaction between form A and form B through hydrogen bonding can in situ generate a bidentate donor ligand in the coordination sphere of a metal (rhodium and platinum) center (Scheme [3]). The present subject can open new gates to the design of self-assembled ligands and can be considered in related chemistries.

Scheme 3 Self-assembly of the 6-DPPon ligand

• References

• 1 Bull JA, Mousseau JJ, Pelletier G, Charette AB. Chem. Rev. 2012; 112: 2642
• 2 Wieland J, Breit B. Nature Chem. 2010; 2: 832
• 3 Breit B, Seiche W. J. Am. Chem. Soc. 2003; 125: 6608
• 4a Gellrich U, Huang J, Seiche W, Keller M, Meuwly M, Breit B. J. Am. Chem. Soc. 2011; 133: 964
• 4b Beierlein CH, Breit B, Paz Schmidt RA, Plattner DA. Organometallics 2010; 29: 2521
• 4c Breit B, Seiche W. Pure Appl. Chem. 2006; 78: 249
• 5 Seiche W, Schuschkowski A, Breit B. Adv. Synth. Catal. 2005; 347: 1488
• 6 Straub AT, Otto M, Usui I, Breit B. Adv. Synth. Catal. 2013; 355: 2071
• 7 Fuchs D, Rousseau G, Diab L, Gellrich U, Breit B. Angew. Chem. Int. Ed. 2012; 51: 2178
• 8 Agabekov V, Seiche W, Breit B. Chem. Sci. 2013; 4: 2418
• 9 Kemme ST, Smejkal T, Breit B. Chem.–Eur. J. 2010; 16: 3423