149879-32-3

Upstream product

• 70258-18-3 2-chloro-5-(chloromethyl)pyridine 
• 2996-92-1 phenyl trimethylsiloxane 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents

The Suzuki–Miyaura cross-coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh3)Cl2] (I) [HL1 = 3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide] as catalyst and K2CO3 as base in neat water. The synthesis of the heterocycle-containing biaryls required the addition of 2 mol-% of a phosphine ligand (PPh3 or X-Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle-containing biaryls, diarylmethanes, and benzophenones in moderate-to-excellent yields.

Palladium nanoparticle catalyzed hiyama coupling reaction of benzyl halides

An efficient Hiyama coupling reaction between benzylic halide and aryltrialkoxysilane using Pd nanoparticles has been developed. This procedure accommodates various functional groups to yield a diverse range of diarylmethanes which are ubiquitous units of natural products and pharmaceuticals.

First cross-coupling reaction of potassium aryltrifluoroborates with organic chlorides in aqueous media catalyzed by an oxime-derived palladacycle

(Chemical Equation Presented) Potassium aryltrifluoroborates are cross-coupled with aryl and heteroaryl chlorides using a 4-hydroxyacetophenone oxime-derived palladacycle as precatalyst, K2CO3 as base, and TBAB as additive in refluxing water under conventional and microwave heating affording the corresponding biphenyls under phosphine-free conditions. For the arylation of allyl and benzyl chlorides, KOH is used as base in acetone-water (3:2) at rt or 50 °C using 0.1 mol % Pd loading providing allylbenzenes and diarylmethanes, respectively.

Suzuki-Miyaura and related cross-couplings in aqueous solvents catalyzed by di(2-pyridyl)methylamine-palladium dichloride complexes

Di(2-pyridyl)methylamine-based palladium dichloride complexes 4 are versatile catalysts for different types of cross-coupling reactions in water or aqueous solvents under aerobic conditions. The Suzuki-Miyaura reaction of arylboronic acids can be performed with bromoarenes under water reflux using K2CO3 as base or at room temperature or 60°C in aqueous methanol using KOH as base. For aryl chlorides the corresponding cross-couplings with arylboronic acids can be carried out in refluxing water with K2CO3 as base and TBAB as additive to provide biaryls and heterobiaryls. Arylboronic acids react with benzylic chlorides and allylic substrates such as chlorides, acetates or carbonates also in refluxing water with K2CO3 as base or at room temperature in aqueous acetone and KOH as base, to give diarylmethanes and arylpropenes. Trimethylboroxine and alkylboronic acids are coupled with bromo- and chloroarenes under water at reflux with K2CO3 as base and TBAB as additive to furnish methyl- and butylarenes. These cross-couplings have also been performed in shorter times under microwave irradiation. Several important intermediates such as, 4′-methylbiphenyl-2-carbonitrile, 4-biphenylacetic acid, 3-(3-methylphenyl)benzoic acid, 4,5-diphenyl-2-methyl- 3(2H)pyridazinone and 2-(4′-fluorobenzyl)thiophene have been prepared under aqueous and aerobic conditions in good yields.

Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles

Palladacycles derived from phenone-oximes 1 are efficient precatalysts for the Suzuki-Miyaura coupling of arylboronic acids with aromatic and heteroaromatic bromides and chlorides under water reflux under aerobic conditions. Alternatively, the coupling can also be carried out at room temperature in methanol-water. Aryl bromides gave biaryls with TON up to 105 and TOF up to 7 × 104 h-1. Activated and deactivated aryl chlorides need the presence of TBAB for the couplings, showing slightly lower efficiency (TON up to 9000 and TOF up to 3850 h-1). C(sp2)-C(sp3) bonds can also be formed by cross-coupling reactions of trimethylboroxine and butylboronic acid with aromatic bromides and chlorides under water reflux and of benzylic and allylic chlorides or acetates with arylboronic acids in acetone-water at room temperature.