14289-95-3Relevant academic research and scientific papers
MERCURY(II) OXIDE/TETRAFLUOROBORIC ACID. AN UNUSUAL BEHAVIOR IN THE OXIDATION OF ALKENES. SYNTHESIS OF trans-CINNAMYLETHERS
Barluenga, Jose,Alonso-Cires, Luisa,Asensio, Gregorio
, p. 2239 - 2240 (1981)
The synthesis of trans-cinnamylethers by oxidation of allylbenzene is described.The reaction cannot be explained by formation of an allylic mercurial.A new type of mechanism in the oxidation of alkenes by mercury(II) salts is proposed.
Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction
Carlet, Federica,Bertarini, Greta,Broggini, Gianluigi,Pradal, Alexandre,Poli, Giovanni
supporting information, p. 2162 - 2168 (2021/04/02)
A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.
Oxidative cleavage of allyl ethers by an oxoammonium salt
Kelly, Christopher B.,Ovian, John M.,Cywar, Robin M.,Gosselin, Taylor R.,Wiles, Rebecca J.,Leadbeater, Nicholas E.
, p. 4255 - 4259 (2015/04/14)
A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.
Step-economy etherification of acylated alcohols
Xu, Hua-Dong,Xu, Ke,Zheng, Qing,He, Wei-Jie,Shen, Mei-Hua,Hu, Wen-Hao
supporting information, p. 6836 - 6838 (2015/01/09)
An efficient and convenient protocol has been developed for ether bond formation in mild conditions. A mixture of primary/secondary ester and allylic/benzylic halide in tetrahydrofuran was treated with KOtBu at room temperature to give ether in high yield. This step economic method enabled direct alkylation of the acyl group masked O-nucleophiles. Application of this method in carbohydrate synthesis was feasible and chemo-selectivity can be achieved.
Regio- and stereoselective Au(I)-catalyzed intermolecular hydroalkoxylation of aryl allenes
Cui, Dong-Mei,Yu, Ke-Rui,Zhang, Chen
scheme or table, p. 1103 - 1106 (2009/09/30)
In the presence of a catalytic amount of Ph3PAuNO3 and H2SO4, the hydroalkoxylation of allenes with alcohols has been shown to proceed smoothly and give allylic ethers in good yields and high regio- and stereoselectivity. Georg Thieme Verlag Stuttgart.
Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination
Nishina, Naoko,Yamamoto, Yoshinori
, p. 4908 - 4911 (2008/09/21)
A wide range of alcohols 2 react with various allenes 1 in the presence of ClAuPPh3/AgOTf catalyst at ambient temperature without solvent to produce allylic ethers 3. Contrary to the hydroamination, which proceeds through high chiral-face selec
o-benzenedisulfonimide as reusable bronsted acid catalyst for acid-catalyzed organic reactions
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano,Venturello, Paolo
, p. 1379 - 1388 (2008/12/21)
Acid-catalyzed organic reactions, such as etherification, esterification, acetal synthesis, cleavage, and interconversion, and pinacol rearrangement were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Bronsted acid catalyst; the conditions were mild and selective. The catalyst was easily recovered and purified, ready to be used in further reactions, with economic and ecological advantages. Georg Thieme Verlag Stuttgart.
A mild and efficient method for the stereoselective formation of C-O bonds: Palladium-catalyzed allylic etherification using zinc(II) alkoxides
Kim, Hahn,Lee, Chulbom
, p. 4369 - 4371 (2007/10/03)
(equation presented) A highly chemo-and stereoselective palladium-catalyzed allylic etherification reaction is described. The use of zinc(II) alkoxides proved effective in promoting the addition of the oxygen nucleophile derived from aliphatic alcohols to η3-allylpalladium complexes. Using diethylzinc (0.5 equiv), 5 mol % of Pd(OAc)2, and 7.5 mol % of 2-di(tert-butyl)phosphinobiphenyl in THF, the cross-coupling reaction between various aliphatic alcohols and allylic acetates proceeded at ambient temperature to furnish allylic ethers with high stereoselectivity.
Palladium-catalyzed coupling of alkynes with alcohols and carboxylic acids
Zhang, Weijiang,Haight, Anthony R.,Hsu, Margaret C.
, p. 6575 - 6578 (2007/10/03)
The palladium-catalyzed coupling of alkynes with alcohols and carboxylic acids to give allylic ethers and esters has been achieved. With phenols, these conditions furnish the C-alkylation products.
Zeolite-HY: A selective and efficient catalyst for the alcoholyses of various alcohols
Gadhwal, Sunil,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.
, p. 1921 - 1927 (2007/10/03)
An efficient and selective method for the conversion of various alcohols into their corresponding ethers in the presence of zeolite under solvolytic condition is described. The reaction proceeds efficiently at ambient pressure in high yields.
