14093-65-3Relevant academic research and scientific papers
Electrochemical properties and reactions of organoboronic acid esters containing unsaturated bonds at their α-position
Ohtsuka, Kazuhiro,Inagi, Shinsuke,Fuchigami, Toshio
, p. G23 - G28 (2017/12/26)
Electrochemical analyses of 2-(cynnamyl)boronic acid pinacol ester and (3-phenyl-2-propynyl)boronic acid pinacol ester, and their trimethylsilyl analogues as well as their parent compounds were comparatively studied by cyclic voltammetry measurements. We
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.
Regioselective and enantioselective iridium-catalyzed allylation of enamines
Weix, Daniel J.,Hartwig, John F.
, p. 7720 - 7721 (2008/02/08)
A highly enantioselective and regioselective monoallylation of the enamines of methyl ketones has been developed. After hydrolysis of the enamine (NaOAc/AcOH(aq)), the desiredallylated ketones were obtained in high yields (64-91% isolated yield
Reaction of orthoesters with alcohols in the presence of acidic catalysts: A study
Sampath Kumar,Joyasawal, Sipak,Reddy,Pawan Chakravarthy,Krishna,Yadav
, p. 1686 - 1692 (2007/10/03)
Allylic and benzylic alcohols are converted into corresponding unsymmetrical ethers when reacted with various orthoesters in the presence of montmorillonite KSF at ambient temperature. A detailed study has been undertaken to examine the mechanism and generality of these reactions with regard to various acidic catalysts, which reveal interesting competitive reactions mainly O-acetylation, together with trace amount of dimerized product. The type of the side product and their relative quantity depends upon the nature of the catalyst employed. Furthermore, the low yields of the Claisen rearrangement product obtained from allylic alcohols under heating is rationalized due to the formation of some of these products.
ENANTIOSELECTIVE AMINATION AND ETHERIFICATION___________________
-
Page 61-62, (2010/02/06)
The present invention is directed to a catalyst composition, comprising: (1) a catalyst precursor having the general structure MSXn wherein M is a transition metal selected from the group consisting of iridium, molybdenum, and tungsten; S is a coordinating ligand; X is a counterion; and n is an integer from 0 to 5; and (2) a phosphoramidite ligand having the structure wherein O-Cn-O is an aliphatic or aromatic diolate and wherein R1, R2, R3 and R4 are selected from the group consisting of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted aliphatic groups, and combinations thereof, with the proviso that at least one of R1, R2, R3, or R4 must be a substituted or unsubstituted aryl or heteroaryl group. The present invention is also directed to activated catalysts made from the above catalyst composition, as well as methods of allylic amination and etherification using the above catalysts.
Synthesis, rearrangement and solvolysis of propargylic and allylic trifluoromethanesulfinates
Braverman, Samuel,Pechenick, Tatiana,Zafrani, Yossi
, p. 51 - 63 (2016/07/15)
The synthesis and reactivity of propargylic and allylic trifluoromethanesulfinates under various conditions has been investigated. Propargylic esters readily undergo [2,3]-sigmatropic rearrangement to the corresponding allenyl trifluoromethyl sulfones, even under solvolytic conditions. An unusually facile nucleophilic addition of the solvent to the allenyl sulfone under the latter conditions has also been observed. On the other hand, the reactivity of allylic esters strongly depends on substitution. Thus, while cinnamyl triflinate reacts by an ionic mechanism, the corresponding α-methylallyl ester reacts by a concerted pathway.
Iodine(III)-Mediated Allylaton of Aromatic Compounds and Alcohols Using Allylmetal (Group IVb) Compounds
Ochiai, Masahito,Fujita, Eiichi,Arimoto, Masao,Yamaguchi, Hideo
, p. 41 - 47 (2007/10/02)
The reaction of allylmetal (group IVb) compounds with aromatic compounds and iodosylbenzene in the presence of BF3-Et2O afforded the corresponding allylation products.Allylation of alcohols was also carried out to give allyl ethers.The activation of iodosylbenzene by the coordination of BF3-Et2O was assumed to be one of the most important factors for the reaction.The involvement of the reactive allyliodine(III) compounds in these reactions is discussed.Keywords - hypervalent organoiodine compound, iodosylbenzene; allylsilane; allylgermane; allylstannane; allyliodine(III) compound
STEREOSELECTIVE FORMATION OF (E)-1-ALKENYL ETHERS. THE COUPLING REACTION OF 1,3- OR 3,3-DIETHOXY-1-PROPENE WITH GRIGNARD REAGENTS CATALYZED BY NICKEL-PHOSPHINE COMPLEX
Sugimura, Hideyuki,Takei, Hisashi
, p. 351 - 354 (2007/10/02)
1,3- or 3,3-Diethpxy-1-propene reacted with Grignard reagents in the presence of nickel-phosphine complex to give (E)-1-alkenyl ethers stereoselectively.
Thallium(III)-Mediated Allylation of Alcohols and Carboxylic Acids: Umpolung of Reactivity of Allylmetal (Group IVb) Compounds
Ochiai, Masahito,Fujita, Eiichi,Arimoto, Masao,Yamaguchi, Hideo
, p. 5027 - 5030 (2007/10/02)
A new general method for the synthesis of allyl ethers and allyl acetates is described.Allylmetal (group IVb) compounds, on treatment with thallium(III) salts in alcohols or acetic acid, gave the corresponding allyl ethers or allyl acetates in good yields.The reaction was successfully applied to the synthesis of the 6-membered cyclic ether 20 via the intramolecular, thallium(III)-mediated allylation reaction of the allylsilane 18.Keywords - allyl ether; allyl acetate; thallium(III) salt; allylsilane; allylstannane; intramolecular cyclization; umpolung
