Addition-elimination reactions of an arylaluminum reagent with vinylarenes is achieved mediated by a rhodium catalyst. The reaction of dimethyl(phenyl)aluminum with a rhodium(I) catalyst takes place to afford (E)-stilbene. The reaction is promoted by the addition of ketone as an additive to give (E)-stilbene in a quantitative yield. A nickel complex bearing cyclopentadienyl (Cp) and N-heterocyclic carbene (NHC) ligands also catalyzes the reaction to afford 1,2-diarylethenes accompanied by a small amount of the saturated byproduct, 1,2-diarylethanes.

Winding vine-shaped molecular asymmetry is induced by enantioselective ring-closing metathesis with a chiral molybdenum catalyst. The reaction proceeds under mild conditions through an E-selective ring-closing metathesis leading to macrocyclic bisazoles with enantioselectivities of up to 96 % ee.

Winding vine-shaped molecular asymmetry is induced by enantioselective ring-closing metathesis with a chiral molybdenum catalyst. The reaction proceeds under mild conditions through an E-selective ring-closing metathesis leading to macrocyclic bisazoles with enantioselectivities of up to 96 % ee.

The reaction of arylacetic acid with aryl halides in the presence of a palladium(0) catalyst proceeds with a Grignard reagent (2 equiv.) to afford diarylated acetic acids. Deprotonation was confirmed by treatment with allyl bromide, which revealed that the use of EtMgCl or tBuMgCl at room temperature to 60 °C resulted in complete deprotonation. After deprotonation of (4-methoxyphenyl)acetic acid under such conditions, the resulting mixture was treated with 4-methoxybromobenzene in the presence of Pd(tBu₃P)₂ (2 mol-%) as a catalyst to give bis(4-methoxyphenyl)acetic acid in 86 % yield. The reaction with several aryl halides under similar conditions gave the corresponding diarylacetic acids.

Rhodium-catalyzed addition/elimination of arylaluminum reagents with vinylarenes was achieved to obtain stilbene derivatives. The reaction of diethyl(phenyl)aluminum with styrene in the presence of the chloro(1,5-cyclooctadiene)rhodium(I) dimer, [RhCl(cod)]₂, and diisopropyl ketone (2,4-dimethyl-3-pentanone) as an additive occurred to give (E)-stilbene in quantitative yield. The use of other arylaluminum reagents afforded β-arylated products in good to excellent yields. This reaction was found to be promoted by ketones as additives, which are reduced to the corresponding alcohols, as confirmed by analysis of the crude reaction mixture by ¹H NMR spectroscopy.

The synthesis of linear and branched oligothiophenes of well-defined structures is performed with regioselective deprotonation of 3-substituted thiophenes and nickel-catalyzed cross-coupling of the thus formed metalated species with a bromothiophene. The reaction of 3-hexylthiophene with EtMgCl and 2,2,6,6-tetramethylpiperidine (TMP-H, 10 mol %) induces the metalation selectively at the 5-position by use of the catalytically generated hindered magnesium amide (TMPMgCl) and the subsequent reaction of a 2-halo-3-hexylthiophene (bromide or chloride) in the presence of a nickel catalyst affords a head-to-tail (HT)-type dimer. By repeating the same sequence, the linear oligothiophene up to a 4-mer is synthesized in good yield. The reaction of 3-hexylthiophene with 2,3-dibromothiophene also takes place to afford a branched oligothiophene 3-mer in quantitative yield. The obtained 3-mer is also metalated at the sterically less-hindered position in a regioselective manner furnishing a 7-mer in >99 % yield after a further coupling reaction with 2,3-dibromothiophene. These dendrimers react with several multifunctionalized organic electrophiles, leading to a variety of branched oligothiophenes.

Tetrakis(triazolylmethyl)ethylenediamine, which is a class of tetrakis(2-pyridylmethyl)ethylenediamine (TPEN) analogue, is synthesized by a quadruple click reaction of tetrapropargylated ethylenediamine and four equivalents of alkyl azide. The obtained compound efficiently extracted the soft metal cadmium(II) ions by solvent extraction. It is also found that an N-isopropylacryl amide (NIPA) gel using the triazole ethylenediamine as a cross-linker exhibits a temperature-dependent extraction performance.