10229-37-5Relevant academic research and scientific papers
Reactions of Tertiary Allylic Amines and Dichlorocarbenes
Wang, Meili,Xiao, Fenfen,Bai, Yinjuan,Hu, Xiangdong
, p. 2259 - 2265 (2015)
In this article, a study on reactions of tertiary allylic amines and dichlorocarbenes had been described. Tertiary allylic amines could result from an interesting de-N-allylation/formylation reaction under the treatment of dichlorocarbenes. Notably, amines containing steric substituents or electron-deficient aromatic substituents on the nitrogen will go through cyclopropanations of the carbon-carbon double bond.
Kinetics and Mechanism of the Gold-Catalyzed Hydroamination of 1,1-Dimethylallene with N-Methylaniline
Carden, Robert G.,Duncan, Alethea N.,Harris, Robert J.,Nakafuku, Kohki,Timmerman, Jacob C.,Widenhoefer, Ross A.
supporting information, p. 10377 - 10386 (2021/06/08)
The mechanism of the intermolecular hydroamination of 3-methylbuta-1,2-diene (1) with N-methylaniline (2) catalyzed by (IPr)AuOTf has been studied by employing a combination of kinetic analysis, deuterium labelling studies, and in situ spectral analysis of catalytically active mixtures. The results of these and additional experiments are consistent with a mechanism for hydroamination involving reversible, endergonic displacement of N-methylaniline from [(IPr)Au(NHMePh)]+ (4) by allene to form the cationic gold π-C1,C2-allene complex [(IPr)Au(η2-H2C=C=CMe2)]+ (I), which is in rapid, endergonic equilibrium with the regioisomeric π-C2,C3-allene complex [(IPr)Au(η2-Me2C=C=CH2)]+ (I′). Rapid and reversible outer-sphere addition of 2 to the terminal allene carbon atom of I′ to form gold vinyl complex (IPr)Au[C(=CH2)CMe2NMePh] (II) is superimposed on the slower addition of 2 to the terminal allene carbon atom of I to form gold vinyl complex (IPr)Au[C(=CMe2)CH2NMePh] (III). Selective protodeauration of III releases N-methyl-N-(3-methylbut-2-en-1-yl)aniline (3 a) with regeneration of 4. At high conversion, gold vinyl complex II is competitively trapped by an (IPr)Au+ fragment to form the cationic bis(gold) vinyl complex {[(IPr)Au]2[C(=CH2)CMe2NMePh]}+ (6).
FLUORESCENT SYNTHETIC RETINOIDS
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Page/Page column 45-46, (2016/05/02)
There are described novel compounds of formula I: which R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each as herein defined.
Cationic Titanocene(III) Complexes for Catalysis in Single-Electron Steps
Gans?uer, Andreas,Hildebrandt, Sven,Michelmann, Antonius,Dahmen, Tobias,Von laufenberg, Daniel,Kube, Christian,Fianu, Godfred D.,Flowers, Robert A.
supporting information, p. 7003 - 7006 (2015/06/08)
Abstract By exploiting solvent and anion effects, [Cp2Ti]+ complexes for atom-economical catalysis in single-electron steps were developed and applied for the first time. These complexes constitute remarkably stable and active cataly
Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)
Orchard, Alexandra,Schamerhorn, Gregory A.,Calitree, Brandon D.,Sawada, Geri A.,Loo, Tip W.,Claire Bartlett,Clarke, David M.,Detty, Michael R.
experimental part, p. 4290 - 4302 (2012/09/08)
Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His 10, to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing
Synthesis of α,α-disubstituted aryl amines by rhodium-catalyzed amination of tertiary allylic trichloroacetimidates
Arnold, Jeffrey S.,Cizio, Gregory T.,Nguyen, Hien M.
supporting information; experimental part, p. 5576 - 5579 (2011/12/04)
The rhodium-catalyzed regioselective amination of tertiary allylic trichloroacetimidates with unactivated aromatic amines is a direct and efficient approach to the preparation of α,α-disubstituted allylic aryl amines in good yield and with excellent regio
Highly efficient and regioselective allylic amination of allylic alcohols catalyzed by [Mo3PdS4] cluster
Tao, Yinsong,Zhou, Yuhan,Qu, Jingping,Hidai, Masanobu
experimental part, p. 1982 - 1984 (2010/06/21)
A highly efficient and regioselective allylation reaction of amines with allylic alcohols under mild conditions catalyzed by the cubane-type sulfido cluster [(Cp*Mo)3S4Pd(dba)][PF6] with H3BO3 as an additive has been developed. A variety of amines and allylic alcohols are investigated, and in the case of allylic alcohols bearing substituents at either α- or γ-position only linear allylic amination products are obtained.
Gold(I)-Catalyzed intermolecular hydroamination of allenes with arylamines
Duncan, Alethea N.,Widenhoefer, Ross A.
experimental part, p. 419 - 422 (2010/04/25)
A mixture of [P(t-Bu)2-o-biphenyl]AuCl and AgOTf catalyzes the intermolecular hydroamination of monosubstituted and 1,1- and 1,3-disubstituted allenes with primary and secondary arylamines. Georg Thieme Verlag Stuttgart · New York.
Amination of allylic alcohols in water at room temperature
Nishikata, Takashi,Lipshutz, Bruce H.
supporting information; experimental part, p. 2377 - 2379 (2009/12/01)
The "trick" to carrying out regiocontrolled aminations of allylic alcohols in water as the only medium is use of a nanomicelle's interior as the organic reaction solvent. When HCO2Me is present, along with the proper base and source of catalytic Pd, allylic amines are cleanly formed at room temperature.
GOLD CATALYZED HYDROAMINATION OF ALKYNES AND ALLENES
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Page/Page column 9/13, (2010/01/29)
Methods are provided for the catalytic hydroamination of compounds having an alkyne or allene functional group, in which the compound is contacted with ammonia or an amine in the presence of a catalytic amount of a gold complex under conditions sufficient for hydroamination to occur.
