Pyridiniump-Toluenesulfonate

Ac, acetyl AIBN, azobis(isobutanonitrile) All, allyl AR, aryl Bn, benzyl f-BOC, ferf-butoxycarbonyl Bu, Butyl Bz, benzoyl CAN, ceric ammonium nitrate Cbz, benzyloxycarbonyl m-CPBA, m-chloroperoxybenzoic acid DAST, diethylaminosulfur trifluoride DBU, l,8-diazabicyclo[5.4.0]undec-7-ene DCC, /V. /V - d i eye I oh e x y I c ar bo -diimide DCM, dichloromethyl DCMME, dichloromethyl methyl ether DDQ, 2,3-dichloro-5,6-dicyano-l,4-benzoquinone DEAD, diethyl azodicarboxylate l-(+)-DET, L-(+)-diethyl tartrate l-DIPT, L-diisopropyl tartrate d-DIPT, D-diisopropyl tartrate DMAP, 4-dimethylaminopyridine DME, 1,2-dimethoxyethane DMF, /V./V-dimethylformamide DMP, 2,2-dimethoxypropane Et, ethyl Im, imidazole KHMDS, potassium hexamethyldisilazane Me, methyl Me2SO, dimethyl sulfoxide MOM, methoxymethyl MOMC1, methoxymethyl chloride Ms, methylsulfonyl MS, molecular sieves NBS, N-bromosuccinimide NIS, /V-iodosuccinimide NMO, /V-methylmorpho-line N-oxide PCC, pyridinium chlorochromate Ph, phenyl PMB, / -methoxvbenzyl PPTs, pyridiniump-toluenesulfonate i-Pr, isopropyl Py, pyridine rt, room temperature TBAF, tetrabutylammonium fluoride TBS, ferf-butyl dimethylsilyl TBDMSC1, f-butylchlorodimethylsilane Tf, trifhioromethylsulfonyl Tf20, trifluoromethylsulfonic anhydride TFA, trifluoroacetic acid THF, tetrahydrofuran TMS, trimethylsilyl TPAP, tetra-n-propylammonium perruthenate / -TsOH. / -toluenesulfonic acid... 

Pyridiniump-toluenesulfonate, f-BuOH or 2-butanone, reflux, 80-99% yield. This method is useful for allylic alcohols. MEM ethers are also cleaved under these conditions. PPTS (f-BuOH, 84°C, 8h, 45% yield) has been used to cleave a MOM in the presence of a PMB group, which is somewhat acid-sensitive. ... 

Silylation of Alcohols, pyridiniump-toluenesulfonate can be used as the catalyst in the silylation of primary and secondary alcohols and phenols (eq 3). Even alcohols sensitive to acid-catalyzed rearrangements can be successfully silylated under these conditions. Continuous removal of the water generated during the reaction is necessary and is achieved via the use of a Soxhlet extractor filled with 4A molecular sieves. 

Kreye and coworkers have utilized CIC lx in their U-4CR for the synthesis of a,fi)-diene monomer 213 (Scheme 7.72) [85]. Employing an acyclic diene metathesis polymerization strategy, the monomers were subsequently polymerized using the second-generation Hoveyda-Gmbbs catalyst in the presence of 1,4-benzoquinone (1,4-BQ) as an additive to obtain compound 214. Hydrogenation followed by the treatment with pyridiniump-toluenesulfonate provided the A -acylindole intermediate 215. Under various conditions, 215 provided polymers containing amide and acid (216,217, and 218) functionalities that can be useful for further modification of the side chain. This method clearly exemplifies that judicious application of IMCRs can lead to a new era in polymer synthesis. 

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