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 intermolecular markovnikov hydroamination of allenes with secondary amines
Xiaoming, Zeng,Soleilhavoup, Michele,Bertrand, Guy
scheme or table, p. 3166 - 3169 (2009/11/30)
A cationic (CAAC)gold(I) complex promotes the addition of all types of nontertiary amines to a variety of alienes, affording allylic amines in good to excellent yields; the amino fragment always adds to the less substituted terminus of the CCC skeleton.
