1335213-07-4

Basic information

• Product Name: 2-(3,5-dimethoxyphenyl)thiophene
• Synonyms: 2-(3,5-dimethoxyphenyl)thiophene
• CAS NO: 1335213-07-4
• Molecular Weight: 220.292
• Mol File: 1335213-07-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(3,5-dimethoxyphenyl)thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,5-dimethoxyphenyl)thiophene(1335213-07-4)
• EPA Substance Registry System: 2-(3,5-dimethoxyphenyl)thiophene(1335213-07-4)

Safety Data

• Hazardous Substances Data: 1335213-07-4(Hazardous Substances Data)

Upstream product

• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 15106-95-3 bis(thien-2-yl)zinc 
• 96-43-5 2-thienyl chloride 
• 192182-54-0 3,5-dimethoxyphenylboronic acid 
• 188290-36-0 thiophene 
• 72470-95-2 3,5-dimethoxybenzenediazonium tetrafluoroborate 
• 10272-07-8 3.5-dimethoxyaniline 
• 6165-68-0 thiophene boronic acid 
• 500-99-2 3,5-dimethoxyphenol 

Relevant articles and documents

Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): New electrophilic coupling partners for room temperature Suzuki-Miyaura cross-coupling reactions

The first cross-coupling reaction between aryl/heteroaryl pentafluorobenzenesulfonates and aryl/heteroaryl boronic acids under mild conditions is described. The successful synthesis of highly ortho substituted biaryls and high chemoselectivity of these bench stable intermediates over tosylates, triflates, mesylates, and chlorides increases its scope as a valuable cross-coupling partner. The generality of this protocol was further extended to other boron containing nucleophiles (boronates, trifluoroborates) and alkyl boronic acids.

Room-temperature Suzuki-Miyaura coupling of heteroaryl chlorides and tosylates

Suzuki-Miyaura coupling of heteroaryls is an important method for the preparation of compound libraries for medicinal chemistry and materials research. Although many catalysts have been developed, none of them have been generally applicable to the coupling reactions of heteroaryl chlorides and tosylates at room temperature. We discovered that a catalyst combination of Pd(OAc)2 and XPhos (2-dicyclohexylphosphanyl-2',4',6'- triisopropylbiphenyl) could efficiently catalyze these couplings. Besides the choice of catalyst, the use of hydroxide bases in an aqueous alcoholic solvent was essential for fast couplings. These conditions promoted fast release of active catalyst (XPhos)Pd0, and accelerated the transmetalation in the catalytic cycle. Most of the major families of heteroaryl chlorides (31 examples) and tosylates (17 examples) reached full conversion within minutes to hours at room temperature. The method could be easily scaled up for gram-scale synthesis. Furthermore, we examined the relative reactivity of coupling partners in whole reactions. Electron-rich heteroaryl chlorides and tosylates reacted more slowly than electron-deficient ones, in the order of indole, pyrrole furan, thiophene > pyridine. Similarly, electron-deficient arylboronic acids were less reactive than electron-neutral and electron-rich ones. The reactivity trends from this study can help to choose appropriate coupling partners for Suzuki reactions.

Erratum: Negishi cross-coupling reaction catalyzed by an aliphatic, phosphine based pincer complex of palladium. biaryl formation via cationic pincer-type PdIV intermediates (Dalton Transactions (2011) 40 (8996) DOI: 10.1039/C1DT10398A)

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