1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry

N-Heterocyclic carbenes (NHC) are nowadays ubiquitous and indispensable in many research fields, and it is not possible to imagine modern transition metal and main group element chemistry without t...

N-Heterocyclic Carbene Adducts of Main Group Elements and Their Use as Ligands in Transition Metal Chemistry.

A series of highly luminescent, heteroleptic copper(I) complexes has been synthesized using a modular approach based on easily accessible P^N ligands, triphenylphosphine, and copper(I) halides, allowing for an independent tuning of the emission wavelength with low synthetic efforts. The molecular structure has been investigated via X-ray analysis, confirming a dinuclear copper(I) complex consisting of a butterfly shaped metal-halide cluster and two different sets of ligands. The bidentate P^N ligand bridges the two metal centers and can be used to tune the energy of the frontier orbitals and therefore the photophysical characteristics, as confirmed by emission spectroscopy and theoretical investigations, whereas the two monodentate triphenylphosphine ligands on the periphery of the cluster core mainly influence the solubility of the complex. By using electron-rich or electron-poor heterocycles as part of the bridging ligand, emission colors can be adjusted, respectively, between yellow (581 nm) and deep b...

Heteroleptic, Dinuclear Copper(I) Complexes for Application in Organic Light-Emitting Diodes

Copper nanoparticles as inexpensive and efficient catalyst: A valuable contribution in organic synthesis

Cu(II) catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles.

Phosphorylation of 1-alkyl substituted imidazoles and benzimidazoles with P(III) halides in pyridine was shown to proceed at the 3-N atom of the heteroaryl ring and was followed by triethylamine-in- duced migration of the phosphorus group to the 2-C atom. Preparative methods were developed for the syn- thesis of a range of 2-phosphorylated derivatives of the indicated imidazoles. The latter were found to undergo alkylation either at P(III) or 3-N centers, depending on the alkylating agent. q 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 585-597, 1999

Phosphorylation of 1‐alkylmidazoles and 1‐alkylbenzimidazoles with phosphorus(III) halides in the presence of bases

1,2-Disubstituted imidazoles react with phosphorus(III) halides in pyridine regioselectively at position 5. The reaction proceeds the more readily, the higher the electron-donating ability of the 2-substituent in the starting imidazole. Hitherto unknown dihalo(imidazol-5-yl)phosphines have been obtained, and their properties have been studied. Also synthetic methods for the preparation of various monohalo(organyl)(imidazolyl)phosphines have been developed. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:289–308, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20550

5-phosphorylated 1,2-disubstituted imidazoles†

4-Selenophosphoryl-1,2-disubstituted imidazoles have been obtained by thermal decomposition of methyl 5-(diamidoselenophosphoryl)imidazolium chlorides. The position of selenophosphoryl group in the imidazole ring was proved by 1H, 13C NMR spectroscopy, and X-ray analysis. Previously unknown diamido- and dichloro(imidazol-4-yl)- phosphonites were synthesized, and differences in their reactivity compared to analogous 5-phosphorylated imidazoles are shown. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:103–118, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20584

4‐Phosphorylated 1,2‐disubstituted imidazoles

The reaction of phosphorus(III) halides with 6-substituted imidazo[2,1-b]thiazoles in the presence of bases proceeds regioselectively and affords 5-phosphinoimidazo[2,1-b]thiazoles, useful synthons for the preparation of various P(III) and P(V) derivatives. 5-Phosphinoimidazo[2,1-b]thiazoles are selectively alkylated at the phosphorus or heterocyclic nitrogen atom, depending on the alkylating agent. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:648–655, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20166

https://www.onlinelibrary.wiley.com/doi/pdf/10.1002/hc.20166

Evgenij V. Zarudnitskii

Papers

Phosphorylation of 1‐alkylmidazoles and 1‐alkylbenzimidazoles with phosphorus(III) halides in the presence of bases

5-phosphorylated 1,2-disubstituted imidazoles†

4‐Phosphorylated 1,2‐disubstituted imidazoles

Phosphorylation of imidazo[2,1‐b]thiazoles with phosphorus(III) halides in the presence of bases

Trimethylsilyl-1,3,4-oxadiazoles—new useful synthons for the synthesis of various 2,5-disubstituted-1,3,4-oxadiazoles