- Sustainable, mild and efficient p-methoxybenzyl ether deprotections utilizing catalytic DDQ
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A procedure for the selective deprotection of p-methoxybenzyl ethers using catalytic amounts of DDQ and of sodium nitrite, with oxygen as the terminal oxidant, is reported.
- Walsh, Katie,Sneddon, Helen F.,Moody, Christopher J.
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p. 7380 - 7387
(2017/09/13)
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- A practical method for p -methoxybenzylation of hydroxy groups using 2,4,6-tris(p -methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM)
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A new acid-catalyzed p-methoxybenzylating reagent, 2,4,6-tris(p- methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM), has been developed. The reaction of acid- and alkali-labile alcohols with TriBOT-PM in the presence of a catalytic amount of various acids (TfOH, BF3·OEt2, CSA, etc.) afforded the corresponding p-methoxybenzyl ethers in good yields. Since TriBOT-PM is an air-stable crystalline solid and can be prepared from inexpensive materials, i.e. cyanuric chloride and anisyl alcohol, this route is of practical use. Georg Thieme Verlag Stuttgart, New York.
- Yamada, Kohei,Fujita, Hikaru,Kitamura, Masanori,Kunishima, Munetaka
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p. 2989 - 2997
(2013/11/06)
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- A convenient approach for the deprotection and scavenging of the PMB group using POCl3
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A convenient and high yielding approach for the deprotection and scavenging of the p-methoxybenzyl (PMB) group in PMB ethers and PMB esters was developed using POCl3 as the reagent. 4-Methoxybenzyl chloride, a starting material used for the preparation of PMB ethers and esters was regenerated in the deprotection step. This mild and selective procedure tolerates several acid sensitive functional groups. The Royal Society of Chemistry 2013.
- Ilangovan, Andivelu,Saravanakumar, Shanmugasundar,Malayappasamy, Subramani,Manickam, Govindaswamy
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p. 14814 - 14828
(2013/09/02)
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- Silver(I)-Catalyzed deprotection of p -methoxybenzyl ethers: A mild and chemoselective method
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The p-methoxybenzyl protecting group (PMB) on various alcohols and an acid was efficiently and selectively cleaved by the action of a catalytic amount of silver(I) hexafluoroantimonate combined with 0.5 equiv of 1,3,5- trimethoxybenzene in dichloromethane at 40 °C.
- Kern, Nicolas,Dombray, Thomas,Blanc, Aurelien,Weibel, Jean-Marc,Pale, Patrick
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p. 9227 - 9235,9
(2012/12/12)
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- Mild, selective deprotection of PMB ethers with triflic acid/1,3-dimethoxybenzene
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An efficient method for the cleavage of the p-methoxybenzyl protecting group of several alcohols in the presence of 0.5 equiv of trifluoromethanesulfonic acid and 1,3-dimethoxybenzene in dichloromethane at room temperature is described.
- Jung, Michael E.,Koch, Pierre
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experimental part
p. 6051 - 6054
(2011/11/28)
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- Reagent for synthesis of para-methoxbenzyl (PMB) ethers and associated methods
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A newly synthesized compound designated lepidine ether 2-(4-Methoxybenzyloxy)-4-methylquinoline reacts with methyl triflate in the presence of alcohols to generate a neutral organic salt that transfers the para-methoxybenzyl (PMB) protecting group onto al
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Page/Page column 3; 4
(2011/06/25)
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- Allylation of 1-phenyl-1-propyne with N- and O-pronucleophiles using polymer supported triphenylphosphine palladium complex as a heterogeneous and recyclable catalyst
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Simple methodology for the allylation of various N- and O-pronucleophiles with 1-phenyl-1-propyne as an allylating agent, using PS-TPP-Pd (polymer supported triphenylphosphine palladium) as a highly active heterogeneous recyclable catalyst has been developed. The protocol is applicable for a wide variety of hindered and functionalized aromatic amines, alcohols, and carboxylic acids. The catalyst exhibited remarkable catalytic activity for five consecutive recycles.
- Wagh, Yogesh S.,Sawant, Dinesh N.,Dhake, Kishor P.,Deshmukh, Krishna M.,Bhanage, Bhalchandra M.
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experimental part
p. 5676 - 5679
(2011/11/06)
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- Pd(OAc)2/dppf as an efficient and highly active catalyst for the allylation of amines, alcohols and carboxylic acids with 1-phenyl-1-propyne
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Pd(OAc)2/1,1′-bis(diphenylphosphino)ferrocene as an efficient, highly active catalyst for the allylation of amines, alcohols and carboxylic acids with 1-phenyl-1-propyne has been developed. The effect of various reaction parameters, such as ligand, time, solvent, temperature, metal: ligand ratio and catalyst concentration on yields of the product were investigated. The optimized procedure works well under mild operating conditions and permits rapid generation of a library for various allylated products.
- Wagh, Yogesh S.,Sawant, Dinesh N.,Tambade, Pawan J.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
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experimental part
p. 2414 - 2421
(2011/04/26)
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- Palladium-catalyzed regio-and enantio-selective allylic substitution reaction of monosubstituted allyl substrates with benzyl alcohols
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Regio-and enantio-selectivities in Pd-catalyzed allylic substitution reaction of monosubstituted allylic substrates with substituted benzyl alcohols were realized, affording the corresponding products in high regioselectivity (up to 93/7) and enantioselec
- Fang, Ping,Ding, Chang-Hua,Hou, Xue-Long,Dai, Li-Xin
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experimental part
p. 1176 - 1178
(2010/11/02)
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