7492-40-2Relevant academic research and scientific papers
Novel access to carbonyl and acetylated compounds: The role of the tetra-: N -butylammonium bromide/sodium nitrite catalyst
Sheykhan, Mehdi,Moafi, Hadi Fallah,Abbasnia, Masoumeh
, p. 51347 - 51355 (2016/06/09)
A novel aerobic oxidation of alcohols without the use of any oxidants was developed. An equimolar catalytic mixture of tetra-n-butylammonium bromide and sodium nitrite catalyzes the aerobic selective oxidation of benzylic alcohols under oxidant-free, base-free and metal-free conditions. The mild reaction conditions allow oxidation of a wide range of benzylic alcohols, chemo-selectively to their carbonyl compounds (68-93% isolated yields). More importantly, high selectivity among different kinds of alcohols (aromatic vs. aliphatic alcohols, primary vs. secondary alcohols as well as alcohols having neutral rings vs. electron-deficient rings) is available by this approach. The method surprisingly switched over to be an efficient acetylation approach in the case of aliphatic alcohols without the use of any transition metal, phosphorous or other toxic reagents or any need for using toxic acyl halides, sulfonyl halides, anhydrides, etc. by the use of only acetic acid as a reagent.
Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp3 C-H cleavage
Lu, Ping,Hou, Tianyuan,Gu, Xiangyong,Li, Pixu
supporting information, p. 1954 - 1957 (2015/04/27)
A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp3 C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.
Solvent-free transesterification in a ball-mill over alumina surface
Chatterjee, Tanmay,Saha, Debasree,Ranu, Brindaban C.
experimental part, p. 4142 - 4144 (2012/08/28)
An efficient procedure for transesterification has been developed in a ball-mill in the absence of any solvent, acid/base or metal catalyst. A variety of methyl, ethyl, allyl esters have been transesterified to higher benzyl and other esters in high yields by this procedure.
Separation, recovery and reuse of N-heterocyclic carbene catalysts in transesterification reactions
Zeng, Tieqiang,Song, Gonghua,Li, Chao-Jun
supporting information; experimental part, p. 6249 - 6251 (2010/02/16)
A novel and convenient strategy to separate, recover and reuse N-heterocyclic carbene catalysts in transesterification reactions has been developed.
Method for producing Suzuki coupling compound catalysed by a nickel compound
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Page 9-11, (2008/06/13)
There are disclosed a method for producing a cross-coupling compound of formula (3):(Y-)(n-1)R1-R2-(R1)(n'-L) ???wherein R1 represents ???a substituted or unsubstituted, linear, branched, or cyclic hydrocarbon group, and ???n and n' each represent 1 or 2, ???provided that when n and n' are the same, both n and n' are not 2, ???R2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group, ???and ???Y represents R2 or X1, wherein R2 is as defined above, and X1 represents a chlorine, bromine or iodine atom, ???which method comprises reacting ???an organic halide of formula (1):n'(R1X1?n), ???wherein R1 is as defined above and carbon atoms at the α and β positions relative to X1 are sp3 carbon atoms, and X1, n and n' are as defined above, ???with a boron compound of formula (2):m{R2(BX2?2)n'}, ???wherein R2 and n' are as defined above, ???X2 independently represents a hydroxyl group or an alkoxy or aryloxy group, or X22 together form an alkoxy or aryloxy group, and m represents 1 or 2, and m≤n, and the boron atom is bonded with an sp2 carbon atom of R2 group, or a boronic acid trimer anhydride thereof, in the presence of a base and a catalyst comprising a nickel compound and a compound of formula (i): ???wherein R3 represents a substituted or unsubstituted alkyl group, ???R4 represents a hydrogen atom or a substituted or unsubstituted alkyl group, ???1 represents an integer of 1 to 3, and ???p and q each represents an integer of 0 to 2; and a catalyst.
ZrCl4 as a mild and efficient catalyst for the one-pot conversion of TBS and THP ethers to acetates
Reddy, Ch. Sanjeeva,Smitha,Chandrasekhar
, p. 4693 - 4695 (2007/10/03)
A mild, efficient and chemoselective method has been developed for the direct transformation of tert-butyldimethylsilyl and tetrahydropyranyl protected alcohols into the corresponding acetates with acetic anhydride and zirconium(IV) chloride as the catalyst in acetonitrile, in a one-pot reaction with high yields and short reaction times. This method has been applied to a variety of substrates.
Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions
Karimi, Babak,Maleki, Jafar
, p. 4951 - 4954 (2007/10/03)
A variety of alcohols and aldehydes were reacted with acetic anhydride at room temperature in the presence of a catalytic amount of lithium triflate (LiOTf) to produce the corresponding esters and 1,1-diacetates, respectively, in good to excellent yields under essentially neutral reaction conditions. Sensitive functional groups such as PhCO2-, OMe, and OTBDMS ethers survived intact under the described reaction conditions.
A fast and practical approach to tetrahydropyranylation and depyranylation of alcohols using indium triflate
Mineno, Tomoko
, p. 7975 - 7978 (2007/10/03)
Indium triflate-mediated tetrahydropyranylation of alcohols in dichloromethane and depyranylation of these products in aqueous methanol utilizing the same reagent but different molar ratio is described. In addition, indium triflate-promoted conversion of tetrahydropyran ethers to their corresponding acetates has also been described.
Facile acetylation of alcohols, ethers and ketals with catalytic FeCl3 in AcOH
Sharma,Mahalingam,Nagarajan,Ilangovan,Radhakrishna, Palakodety
, p. 1200 - 1202 (2007/10/03)
A simple and efficient protocol for the conversion of alcohols, ethers and ketals to acetates using catalytic FeCl3(5mol%) in AcOH, or AcOH (3eq) in CH2Cl2 in very high yield is reported. A variety of other acids such as CF3CO2H, HCO2H, CH2=CHCO2H, CH3CH2CO2H, CH3(CH2)2CO2H have also been utilised for the acylation of alcohols successfully.
