71104-84-2Relevant academic research and scientific papers
Catalytic Use of Elemental Gallium for Carbon-Carbon Bond Formation
Qin, Bo,Schneider, Uwe
supporting information, p. 13119 - 13122 (2016/10/25)
The first catalytic use of Ga(0) in organic synthesis has been developed by using a Ag(I) cocatalyst, crownether ligation, and ultrasonic activation. Ga(I)-catalyzed C-C bond formations between allyl or allenyl boronic esters and acetals, ketals, or aminals have proceeded in high yields with essentially complete regio- and chemoselectivity. NMR spectroscopic analyses have revealed novel transient Ga(I) catalytic species, formed in situ through partial oxidation of Ga(0) and B-Ga transmetalation, respectively. The possibility of asymmetric Ga(I) catalysis has been demonstrated.
Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals
Ito, Suguru,Hayashi, Akira,Komai, Hirotomo,Yamaguchi, Hitoshi,Kubota, Yoshihiro,Asami, Masatoshi
, p. 2081 - 2089 (2011/04/19)
A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity.
Mesoporous aluminosilicate-catalyzed Sakurai allylation and Mukaiyama aldol reaction of acetals
Ito, Suguru,Hayashi, Akira,Komai, Hirotomo,Kubota, Yoshihiro,Asami, Masatoshi
experimental part, p. 4243 - 4245 (2010/09/07)
In the presence of a catalytic amount of mesoporous aluminosilicate (Al-MCM-41), both allyltrimethylsilane and silyl enol ether reacted with various acetals under mild reaction conditions to afford the corresponding homoallyl ethers and β-alkoxy ketones,
Unexpected Lewis acid mediated reactions of 1-arylbut-3-en-1-ols with trimethyl orthoformate - A new synthesis of homoallyl ethers and chlorides
Meri?or, Elena,Conrad, Jürgen,Malakar, Chandi C.,Beifuss, Uwe
, p. 903 - 907 (2008/12/22)
1-Arylbut-3-en-1-ols react with trimethyl orthoformate in the presence of Lewis acids like InCl3, BiCl3, TiCl4, or BF3·OEt2 providing homoallyl ethers or homoallyl chlorides in high yields. Georg Thieme Verlag Stuttgart.
Trimethylsilyl trifluoromethanesulfonate catalyzed one-pot method for the conversion of aldehydes to homoallyl ethers in an ionic liquid
Anzalone, Peter W.,Mohan, Ram S.
, p. 2661 - 2663 (2007/10/03)
A mild method for the trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed one-pot synthesis of homoallyl ethers from aldehydes has been developed in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([bmim] [OTf]). The advanta
Bismuth compounds in organic synthesis. A one-pot synthesis of homoallyl ethers and homoallyl acetates from aldehydes catalyzed by bismuth triflate
Anzalone, Peter W.,Baru, Ashvin R.,Danielson, Eric M.,Hayes, Patrick D.,Nguyen, Mai P.,Panico, Ambrose F.,Smith, Russell C.,Mohan, Ram S.
, p. 2091 - 2096 (2007/10/03)
(Chemical Equation Presented) Three one-pot methods for the conversion of aldehydes to homoallyl ethers catalyzed by Bi(OTf)3? xH 2O (1 x 4) have been developed. The one-pot synthesis of homoallyl ethers can be achieved either by
Iron(III) chloride-catalyzed convenient one-pot synthesis of homoallyl benzyl ethers starting from aldehydes
Watahiki, Tsutomu,Akabane, Yusuke,Mori, Seiji,Oriyama, Takeshi
, p. 3045 - 3048 (2007/10/03)
(Matrix presented) Iron(III) chloride-catalyzed effective allylation reactions of acetals with allyltrimethylsilane proceeded smoothly in high to excellent yields. In addition, this method could be applied to the one-pot synthesis of homoallyl benzyl ethe
Scandium triflate catalyzed allylation of acetals and gem-diacetates: A facile synthesis of homoallyl ethers and acetates
Yadav, Jhillu S.,Subba Reddy, Basi V.,Srihari
, p. 673 - 675 (2007/10/03)
Scandium triflate catalyzes efficiently the allylation reactions of acetals and gem-diacetates with allyltrimethylsilane at ambient temperature to afford the corresponding homoallyl ethers and acetates in high yields. Also it is found to be effective for
Kinetics of the reactions of carboxonium ions and aldehyde boron trihalide complexes with alkenes and allylsilanes
Mayr, Herbert,Gorath, Gorden
, p. 7862 - 7867 (2007/10/02)
Second order rate constants for the reactions of carboxonium ions Ar(MeO)CH+ and aldehyde-boron trihalide complexes ArCH=O→BX3 with allylsilanes and alkenes have been determined in CH2Cl2 solution. The relative reactivities of these electrophiles are almost independent of the nature of the π-nucleophiles, and it is possible to give an averaged reactivity order. For the electrophiles PhCH=O→BF3, PhCH=O→BCl3, Ph(p-MeOC6H4)CH+, and Ph(MeO)CH+, i.e., for PhCHX+ with X = F3BO-, Cl3BO-, p-MeOC6H4, MeO relative averaged reactivities of 1 : 5 × 102 : 1 × 104 : 4 ×105 (CH2Cl2, -70 °C) are determined indicating that the electrophilicities of aldehydeBHal3 complexes are only 3-6 orders of magnitude smaller than those of the corresponding carboxonium ions. The α-methoxy substituted benzyl cations Ar(MeO)CH+ are 3-16 times more reactive (CH2Cl2, 20 °C) than their phenylogous benzhydryl analogues Ar(P-MeOC6H4)CH+.
