600732-10-3

Upstream product

• 107-85-7 1-amino-3-methylbutane 
• 122-78-1 phenylacetaldehyde 
• 18640-74-9 2-isobutylthiazole 
• 108-90-7 chlorobenzene 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 

Relevant academic research and scientific papers

Palladium-catalyzed direct arylation of thiazoles with aryl bromides

Thiazole, 2-phenyl or -alkyl substituted one and benzothiazole are efficiently arylated with aryl bromides at the 2- and/or 5-position(s) in the presence of Pd(OAc)2 and a bulky phosphine ligand using Cs2CO3 as base. 2-Phenyl-5-thiazolecarboxanilide undergoes successive diarylation at the 4- and 5-positions accompanied by decarbamoylation.

C[sbnd]H Bond activation of 2-isobutylthiazole at C5 position catalysed by Pd-N-heterocyclic carbene complexes

A highly efficient and effective protocol has been developed for the synthesis of C5-(hetero)arylated 2-isobutylthiazole derivatives. Four different palladium N-heterocyclic carbene (Pd-NHCs) complexes [Pd(μ-Cl)Cl(SIMes)]2 (2), (LCl2Pd-SIMes) (3: L = PPh3; 4: L = Py; 5: L = 3-CHO-Py) were synthesized and used for the first time as a catalysts in direct C-H arylation reaction of 2-isobutylthiazole at C5 position. Utilizations of these catalytic systems, the arylation of 2-isobutylthiazole with substituted (hetero)aryl bromides efficiently proceeded at low catalyst loading (1mol%) and without any additives such as PivOH under argon or aerobic conditions at 120 °C in a short time. Different substituted (hetero)aryl bromides, even some deactivated or highly sterically hindered (hetero)arylbromides, with a wide range of functional groups were successfully utilized under the optimum reaction conditions. In all cases, the C5 arylated 2-isobutylthiazoles were obtained in moderate to excellent yields.

Pd-N-heterocyclic carbene complex catalysed C-H bond activation of 2-isobutylthiazole at the C5 position with aryl bromides

An effective and efficient catalytic system has been reported for the synthesis of C5-arylated 2-isobutylthiazoles. Pd-N-heterocyclic carbene complexes like [Pd(μ-Cl)Cl(SIPr)]2(2) and (LCl2Pd-SIPr) (3:L= PPh3,4:L= Py;5:L= 3-CHO-Py) were synthesized and characterized by1H,13C,31P NMR, LC-MS/MS, elemental analysis, and FTIR spectroscopy. These Pd-N-heterocyclic carbene complexes were assessed for the first time as catalysts for the C-H arylation reaction of 2-isobutylthiazole at the C5 position with different (hetero)aryl bromides. The catalytic system showed a low catalyst loading (1 mol%) and did not require the use of additional additives such as pivalic acid. The catalytic system developed with these catalysts enables the synthesis of fine chemicals in high yields under aerobic or anaerobic conditions. All complexes showed moderate to good yields in the C5 direct arylation of 2-isobutylthiazole, while complex2exhibited higher catalytic activity than the other complexes.

Cu-Catalyzed Aerobic Oxidative Sulfuration/Annulation Approach to Thiazoles via Multiple Csp3-H Bond Cleavage

A novel and practical Cu-catalyzed aerobic oxidative synthesis of thiazoles was developed. This chemistry for the first time achieved thiazole construction from simple aldehydes, amines, and element sulfur through multiple Csp3-H bond cleavage processes. Molecular oxygen was used as a green oxidant in this oxidative protocol. The substrate scope is broad with the tolerance of aliphatic amines. The mechanistic study might promote the reaction design for a new sulfuration/annulation reaction with readily available element sulfur.

Establishment of broadly applicable reaction conditions for the palladium-catalyzed direct arylation of heteroatom-containing aromatic compounds

Conditions for the palladium-catalyzed direct arylation of a wide range of heterocycles with aryl bromides are reported. Those conditions employ a stoichiometric ratio of both coupling partners, as well as a substoiehiometric quantity of pivalic acid, which results in significantly faster reactions. An evaluation of the influence of the nature of the aryl halide has also been carried out.

Direct arylation of thiazoles on water

Wetter is better: The direct arylation of thiazoles on water is quicker, cleaner, and higher-yielding than arylation in organic solvents. The reaction works under mild conditions for an array of aryl iodides, producing 2,5-diaryl thiazoles in excellent yields. Importantly, novel bi-heteroaryl compounds are produced without the requirement for stoichiometric organometallic coupling agents. (Figure Presented).