115419-49-3Relevant academic research and scientific papers
The chemistry of pentavalent organobismuth reagents. Part 14. Recent advances in the copper-catalyzed phenylation of amines
Arnauld, Thomas,Barton, Derek H.R.,Doris, Eric
, p. 4137 - 4144 (1997)
A reinvestigation of the copper-mediated phenylation of amines by Bi(V) reagents is reported. The influence of the ligands bound to bismuth and the basicity of the amines have been examined. These results, combined with our previous observations, led to the development of a new system for the quantitative phenylation of selected hindered aliphatic and aromatic amines.
B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of: In situ -formed enamines
Wu, Rongpei,Gao, Ke
, p. 4032 - 4036 (2021/05/19)
A highly efficient B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines in the presence of water and pinacolborane was developed. Regioselective β-deuteration of tertiary amines was achieved with high chemo- and regioselectivity. D2O was used as a readily available and cheap source of deuterium. Mechanistic studies indicated that B(C6F5)3 could activate water to promote the protonation and reduction of enamines. This journal is
Reductive N-Arylethylation of Aromatic Amines and N-Heterocycles with Enol Ethers
V?gerl, Katharina,Ong, Duc Nghia,Bracher, Franz
, p. 1323 - 1330 (2017/12/26)
A convenient method for N-arylethylation of aromatic amines and heterocycles under mild reductive conditions was developed using (2-methoxyvinyl)(hetero)arenes as building blocks and triethylsilane/trifluoroacetic acid as reducing agent. This protocol is compatible with numerous functional groups, and aliphatic amines are inert due to protonation.
A simple and convenient method for the synthesis of N, N-diaryl tertiary amines
Wekesa, Francis S.,Phadke, Neha,Jahier, Claire,Cordes, David B.,Findlater, Michael
, p. 1046 - 1051 (2014/05/06)
Direct preparation of tertiary amines in which two substituents are aromatic is described. In the presence of either the inorganic base sodium tert-butoxide or the sterically hindered organic base diisopropylethylamine, the alkylation of secondary diarylamines is achieved smoothly. In contrast to methods previously reported in the literature, this procedure is high-yielding and does not require the use of transition-metal catalysts or functional-group-intolerant hydride reductants. Georg Thieme Verlag Stuttgart ? New York.
Efficient palladium-catalyzed amination of aryl chlorides using dicyclo-hexylamino[(2,6-dimethyl)morpholino]phenylphosphine as a PN2 ligand
Park, Song-Eun,Kang, Seung Beom,Jung, Kwang-Ju,Won, Ju-Eun,Lee, Sang-Gyeong,Yoon, Yong-Jin
experimental part, p. 815 - 823 (2009/07/11)
The palladium-catalyzed amination of aryl chlorides with various amines is accomplished using dicyclohexyl- amino[(2,6-dimethyl)morpholino]phenylphosphine as a bulky electron-rich monoaryl phosphine ligand. The optimized reaction conditions required the use of 1 mol% each of catalyst and ligand. Georg Thieme Verlag Stuttgart.
Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids
Liu, Zhijian,Larock, Richard C.
, p. 3198 - 3209 (2007/10/03)
An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl inflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.
Water-Tolerant Unstabilized Carbanion Equivalents: Bismuth(III) Chloride-Aluminum Promoted Alkylations of Immonium Cations to Amines in Aqueous Media
Katritzky, Alan. R.,Shobana, Navayath,Harris, Philip A.
, p. 4247 - 4248 (2007/10/02)
In the presence of bismuth(III) chloride-metallic aluminum, alkyl as well as allyl halides react with N-(alkylamino)benzotriazoles at 20 deg C in THF-water to give the corresponding homoalkylated amines in high yields.
ALKYLATION OF AMINES USING TRIVALENT BISMUTH DERIVATIVES
Barton, Derek H. R.,Ozbalik, Nubar,Ramesh, Manian
, p. 857 - 860 (2007/10/02)
Mixed alkylaryl Bi(III) derivatives have been prepared by both anionic and free radical methods.The thermal stability of these compounds permits them to be used in the presence of cupric acetate for alkylation of amines.Trialkylbismuth compounds can also be used in the same way.
