404586-95-4Relevant articles and documents
Anionic Fries rearrangement of aryl carbonates. A facile route to ortho-hydroxy esters
Ananin, Aleksei V.,Kraus, George A.
supporting information, (2020/10/13)
Aryl carbonates react with LDA or LiTMP to produce ortho-hydroxy esters.
MgBr 2 · OEt 2: A Lewis Acid Catalyst for the O - And N -Boc Protection of Phenols and Amines
Schechter, Aaron,Goldrich, David,Chapman, Jessica R.,Uberheide, Beatrix M.,Lim, Daniel
supporting information, p. 653 - 660 (2015/10/29)
MgBr2 · OEt2 efficiently catalyzes the O- and N-tert-butoxycarbonylation of functionalized phenols and amines. The presented procedure is operationally simple and done under solvent-free conditions. GRAPHICAL ABSTRACT.
A new, efficient, and catalyst-free microwave-assisted approach for formation of O-tert-butoxy carbonates
K'tir, Hacene,Amira, Aicha,Berredjem, Malika,Aouf, Nour-Eddine
supporting information, p. 851 - 853 (2014/06/23)
A new simple, efficient, greener, and catalyst-free chemoselective protocol for the O-tert-butoxycarbonylation of various structurally diverse hydroxy compounds was carried out with (Boc)2O under microwave radiation. The corresponding O-tertbutoxy carbonates were obtained in good to excellent yields in a short reaction time without any side reactions.
Mixed metal MgO-ZrO2 nanoparticle-catalyzed O-tert-Boc protection of alcohols and phenols under solvent-free conditions
Gawande, Manoj B.,Shelke, Sharad N.,Branco, Paula S.,Rathi, Anuj,Pandey, Rajesh K.
experimental part, p. 395 - 400 (2012/09/25)
An environmentally benign method for O-tert-Boc protection of alcohols and phenols catalyzed by MgO-ZrO2 nanoparticles under solvent-free conditions is described. A variety of phenols, alcohols (aliphatic and aromatic) were converted to corresponding O-tert-Boc products in good to excellent yield (50-95%). The present protocol is expedient, simple, and efficient under solvent-free conditions. The MgO-ZrO2 Nps are easily prepared from inexpensive precursors, and are reusable, recyclable and chemoselective. Copyright 2012 John Wiley & Sons, Ltd. Copyright
Nickel catalyzed cross-coupling of aryl C-O based electrophiles with aryl neopentylglycolboronates
Leowanawat, Pawaret,Zhang, Na,Percec, Virgil
experimental part, p. 1018 - 1025 (2012/03/22)
The efficiency of mesylates, sulfamates, esters, carbonates, carbamates, and methyl ethers as C-O-based electrophiles attached to the 1- or 2-position of naphthalene and to activated and nonactivated phenyl substrates was compared for the first time in Ni-catalyzed cross-coupling with phenyl neopentylglycolboronates containing electron-rich and electron-deficient substituents in their para-position. These experiments were performed in the presence of four different Ni(II)- and Ni(0)-based catalysts. Ni(II)-based catalysts mediate the cross-coupling of most 2-naphthyl C-O electrophiles with both arylboronic acids and with neopentylglycolboronates when K 3PO4 is used as base. The same catalysts are not efficient when CsF is used as base. However, Ni(0)-based catalysts exhibit selective efficiency, and when reactive, their efficiency is higher than that of Ni(II)-based catalysts in the presence of both K3PO4 and CsF. These results provide both reaction conditions for the cross-coupling, and for the elaboration of orthogonal cross-coupling methodologies of various C-O based electrophiles with aryl neopentylglycolboronates. With the exception of mesylates and sulfamates the efficiency of all other 2-naphthyl C-O electrophiles was lower in cross-coupling with aryl neopentylglycolboronates than with arylboronic acids
An eco-sustainable erbium(iii)-catalyzed method for formation/cleavage of O-tert-butoxy carbonates
Procopio, Antonio,Cravotto, Giancarlo,Oliverio, Manuela,Costanzo, Paola,Nardi, Monica,Paonessa, Rosina
experimental part, p. 436 - 443 (2011/04/17)
A new simple and effective method for the formation/cleavage of O-tert-butoxy carbonates of alcohols and phenols is proposed. Mesoporous silica-supported Er(iii) (ErIII-MCM-41) was used as an efficient and reusable solid catalyst in the solvent-free ultrasound-assisted synthesis of Boc-carbonate derivatives of a wide range of alcohols and phenols. The fast, selective deprotection of Boc-derivatives is achieved with a very low amount of Er(OTf)3 in ethanol under microwave irradiation. Therefore, the entire protection/de-protection process is very attractive, from the point of view of sustainability.
An eco-sustainable erbium(III) triflate catalyzed formation and cleavage of tert -butyl ethers
Procopio, Antonio,Costanzo, Paola,Curini, Massimo,Nardi, Monica,Oliverio, Manuela,Paonessa, Rosina
supporting information; experimental part, p. 73 - 78 (2011/03/19)
An eco-compatible method, which permits the formation or cleavage of tert-butyl ethers of alcohols and phenols, is proposed. The protection step is performed in solvent-free conditions at room temperature using catalytic amount of Er(OTf)3. The catalyst is easily- recovered from the aqueous phase and reused several times without significant loss of activity. The deprotection step developed is also highly eco-friendly since the tert-butyl group is removed very quickly from alcohols and phenols in methanol using MW irradiation-. Georg Thieme Verlag Stuttgart · New York.
Chemoselective O-tert-butoxycarbonylation of phenols using 6,7-dimethoxyisoquinoline as a novel organocatalyst
Saito, Yukako,Yoshimura, Yuichi,Takahata, Hiroki
experimental part, p. 6915 - 6917 (2011/03/18)
The chemoselective O-tert-butoxycarbonylation of phenols using low levels (5-0.1 mol %) of 6,7-dimeth-oxyisoquinoline as a reusable organocatalyst is described.
Facile tert-butoxycarbonylation of alcohols, phenols, and amines using BiCl3 as a mild and efficient catalyst
Suryakiran,Prabhakar,Venkateswarlu
, p. 177 - 185 (2008/03/17)
Facile tert-butoxycarbonylation of alcohols, phenols, and amines is described by treatment of alcohols, phenols, and amines with di-tert-butyl dicarbonate in the presence of a catalytic amount of bismuth(III) chloride, a mild and efficient catalyst, at room temperature in excellent yields. Copyright Taylor & Francis Group, LLC.
