49772-02-3

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 811-98-3 d⁽⁴⁾-methanol 
• 49772-01-2 2.4.6-trimethoxyphenyl silver 
• 758-12-3 deuteroacetic acid 
• 1131-40-4 2-bromo-1,3,5-trimethoxybenzene 

Relevant academic research and scientific papers

Scandium trifluoromethanesulfonate as catalyst in the hydrogen/deuterium exchange of 1,3,5-trimethoxybenzene: Evidence for a direct interaction of scandium with the aromatic ring

Scandium trifluoromethanesulfonate in CD3OD is a very active catalyst for hydrogen/deuterium exchange at the aromatic nucleus of 1,3,5-trimethoxybenzene. The very low proticity of the system, spectrophotometric evidence, and easy iodination of

Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides

Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.

Hydroxy- and Methoxybenzene Derivatives with Benzenediazonium Salts ― Chemical Behavior and Tautomeric Problems

The azo-coupling reactions between 4-nitrobenzenediazonium tetrafluoroborate and a series of benzene derivatives bearing at least one electron-donating hydroxy or methoxy substituent have been studied. Depending on the nucleophile and its relative ratio with the diazonium salt, it was possible to obtain mono- and disubstituted products as well as a trisubstituted product for phloroglucinol. The reactions between 3,5-diaminoanisole or 3,5-diaminophenol derivatives and 2 equiv. of diazonium salt gave the monosubstituted product in the first case and a diadduct in the second case; X-ray diffraction analysis revealed a highly symmetric structure for the latter. The different behaviors of hydroxy- and methoxy-substituted compounds was particularly evident for phloroglucinol and 1,3,5-trimethoxybenzene and may be rationalized on the basis of the different electronic effects of the substituents. The propensities of the aromatic rings to undergo H/D exchange reactions were investigated for a series of substrates, and a comparison of the results obtained provided new insights into this phenomenon and permitted a better explanation of the findings reported here; a new particular interaction competes with the formation of a proton–phloroglucinol σ complex.

Proton-catalysed E-Z isomerisation and Pd(II) assisted carbon-carbon cleavage on 3-phenyl-4-(2,4,6-trimethoxyphenyl)methyleneisoxazolin-5-one

Proton electrophilic addition to 3-phenyl-4-(2,4,6-trimethoxyphenyl)-methyleneisoxazolin-5-one can either catalyse E-Z isomerisation or a Pd(II) assisted cleavage of the exocyclic sp2-hybridised C-C bond in dependence on the proton site attack.

Synthesis and characterization of sterically hindered arylsilanes containing the 2,4,6-trimethoxyphenyl ligand (TMP): X-ray structures of (TMP)SiH3, (TMP)2SiH2, and (TMP)3SiH

The homologous series of primary, secondary and tertiary silanes containing the sterically demanding 2,4,6-trimethoxyphenyl (TMP) group have been prepared in yields ranging from 22 to 45%. The arylsilanes were characterized by multinuclear NMR, IR, GC-MS,