Isomerization of cyclohexane and hexane over silica- embedded triflate derivative catalysts

Gagea, Bogdan C.; Parvulescu, Andrei‐Nicolae; Parvulescu, VI; Grange, P.; Poncelet, Georges

doi:10.3998/ark.5550190.0003.205

Cited by 3 publications

(1 citation statement)

References 19 publications

(23 reference statements)

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“…5c Application of the Lewis acid tert -butyl dimethylsilyltrifluoromethane sulfonate has been reported to produce ortho - tert -butylated phenols and naphthols, but again with poor regiocontrol. 5d e More recently, ortho - tert -butylation of aryl methyl ethers have been studied by deploying Keggin tungstophosphoric acid (H 3 PW 2 O 40 ) or Santa Barbara Amorphous clay (SBA-15) in conjunction with similar tert -butyl cation precursors, and all have illuminated similar regiocontrol problems. 5f Given these and many other studies, it should be apparent to all that cationic alkylation regimes fail to provide much synthetic utility.…”

Section: Friedel–crafts Alkylationmentioning

confidence: 99%

Strategies for ortho-tert-Butylation of Phenols and their Analogues

Pettus¹,

Chan²

2022

Synlett

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A new general process for constructing ortho-tert-butyl phenols is presented within the context of other known methods. All are briefly evaluated with regards to regioselectivity, efficiency, and functional group tolerance. In addition, we present an assortment of tert-butyl substrates accessed through o-QM chemistry. Our conclusion is that the o-QM process provides greater yields, flexibility, and generality than most other known methods for delivering ortho-tert-buytlated phenols and their derivatives.1 Introduction2 Friedel–Crafts Alkylation3 Addition of t-Bu– or t-Bu• to Carbonyl Compounds4 ipso-SNAr Reactions of Aryl Methoxy and tert-Butylsulfoxide Moieties5 Metal-Mediated Coupling of Aryl Bromides6 Applications of o-Quinone Methides (o-QMs)7 Conclusion

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