2005
DOI: 10.1016/j.jfluchem.2005.03.010
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Rare earth(III) perfluorooctanesulfonates catalyzed Friedel–Crafts alkylation in fluorous biphase system

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Cited by 36 publications
(15 citation statements)
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“…Although various methods for the preparation of such compounds have been reported with the use of a range of catalysts such as metal triflates, H 2 SO 4 , NbCl 5 , I 2 , surfactant‐type Brønsted acids, amberlyst‐15, pentafluorophenylboronic acid, and NaHSO 4 /SiO 2 , the substrate scope has not yet been thoroughly investigated . Recently, we developed a general method for the SnBr 4 ‐promoted Friedel–Crafts‐type dehydrative alkylation of diarylmethanols 1 with 2‐naphthol derivatives to yield 2 under mild conditions by adjusting the catalyst loading and the reaction temperature according to the electronic nature of the substrates (Scheme , part 1) …”
Section: Introductionmentioning
confidence: 99%
“…Although various methods for the preparation of such compounds have been reported with the use of a range of catalysts such as metal triflates, H 2 SO 4 , NbCl 5 , I 2 , surfactant‐type Brønsted acids, amberlyst‐15, pentafluorophenylboronic acid, and NaHSO 4 /SiO 2 , the substrate scope has not yet been thoroughly investigated . Recently, we developed a general method for the SnBr 4 ‐promoted Friedel–Crafts‐type dehydrative alkylation of diarylmethanols 1 with 2‐naphthol derivatives to yield 2 under mild conditions by adjusting the catalyst loading and the reaction temperature according to the electronic nature of the substrates (Scheme , part 1) …”
Section: Introductionmentioning
confidence: 99%
“…We prepared Yb(OPf) 3 from ytterbium oxide (Yb 2 O 3 ) by stirring it with heptadecafluorooctanesulfonic acid (R f8 SO 3 H, PfOS) (Scheme 1) according to the previously reported method [18][19][20][21][22][23]. To select our catalytic system, we took into account that the ytterbium catalyst has to be fixed onto a polymer, possibly by chelation.…”
Section: Preparation Of A-21-yb(opf)mentioning
confidence: 99%
“…In previous research on lanthanide perfluorooctanesulfonate catalyzed reactions, we found that the reported ytterbium perfluorooctanesulfonate [Yb(OPf) 3 ] is an efficient and relatively cheap catalyst for various organic reactions such as Fridel-Crafts alkylation [18] and acylation [19,20], esterification [21], nitration [22][23][24], and aldol condensation [25] in fluorous biphasic system. Taking concerns on fluorous solvents into consideration, we decided to concentrate on developing a supported-Yb(OPf) 3 catalytic system which is highly active and stable for organic reactions.…”
Section: Introductionmentioning
confidence: 99%
“…The crude product adsorbed on silica gel was transferred onto a short silica gel column. Elution with PE gave the desired 1benzyl-4-fluorobenzene (4b) 13 as a colourless oil; yield: 12.02 g (88%). 1 The characterisation data for the compounds listed in Table 1 can be found in reference 10.…”
Section: Procedures 2 Gram-scale Synthesis Of 1-benzyl-3-nitrobenzene mentioning
confidence: 99%