41605-90-7Relevant academic research and scientific papers
Catalyst-free photodecarbonylation ofortho-amino benzaldehyde
Li, Lamei,Wang, Songping,Wei, Wentao,Yan, Ming,Zhou, Jingwei
, p. 3421 - 3426 (2020/06/25)
It is almost a consensus that decarbonylation of the aldehyde group (-CHO) needs to not only be mediated by transition metal catalysts, but also requires severe reaction conditions (high temperature and long reaction time). In this work, inspired by the “conformational-selectivity-based” design strategy, we broke this consensus and discovered a catalyst-free photodecarbonylation of the aldehyde group. It revealed that decarbonylation can be easily achieved with visible light irradiation by introducing a tertiary amine into theortho-position of the aldehyde group. A diverse array of tertiary amines is tolerated by our photodecarbonylation under mild conditions. Furthermore, the (QM) computations of the mechanism and the experiments on well-designed special substrates revealed that our photodecarbonylation depends on the conformational specificity of the aldehyde group and tertiary amine, and occurs through an unusual [1,4]-H shift and a subsequent [1,3]-H shift.
N-heterocyclic carbene-Pd(II)-2-methyl-4,5-dihydrooxazole complex-catalyzed highly chemoselective mono-amination of dichlorobenzenes
He, Qian-Wei,Lu, Jian-Mei,Shao, Li-Xiong,Sun, Kai-Xin,Zhou, Jin-Hui
, (2020/01/22)
The palladium-catalyzed chemoselective mono-amination of dichlorobenzenes was reported in this paper. Under the suitable conditions, all reactions involving the three isomers of dichlorobenzenes with various secondary and primary amines in the presence of
Photo-induced dealdehyding method
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Paragraph 0048-0059, (2020/06/16)
The invention provides a photo-induced dealdehyding method, and belongs to the technical field of organic synthesis. The photo-induced dealdehyding method comprises the following steps that a mixtureof a compound shown in the formula I and a solvent are reacted under an inert gas atmosphere and visible light irradiation, a dealdehyding product is obtained, and no photocatalyst is used in the whole process; wherein the structural formula of the formula I shown in the specification, R is a functional group and is selected from hydrogen, methyl, methoxyl, cyano, chlorine, bromine or fluorine. According to the photo-induced dealdehyding method, in the inert gas atmosphere, the compound shown in the formula (I) can be excited to generate carbon-oxygen bond homogeneous cracking through visiblelight irradiation, then free radical migration and double bond displacement are conducted, finally carbon monoxide is removed, aldehyde group removal is completed, no photocatalyst is needed in the whole process, operation is easy and convenient, and conditions are mild.
METHODS FOR FORMING ARYL CARBON-NITROGEN BONDS USING LIGHT AND PHOTOREACTORS USEFUL FOR CONDUCTING SUCH REACTIONS
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Paragraph 0097-0098; 0158-0159, (2019/11/22)
The disclosure relates to a method for forming aryl carbon-nitrogen bonds and to photoreactors useful in these and other light-driven reactions. The method comprises contacting an aryl halide with an amine in the presence of a Ni salt catalyst solution and an optional base, thereby forming a reaction mixture; exposing the reaction mixture to light under reaction condition sufficient to produce the aryl carbon-nitrogen bonds. In certain embodiments, the amine may be present in a molar excess to the aryl halide. In certain embodiments, the Ni salt catalyst solution includes a Ni(II) salt and a polar solvent, wherein the Ni(II) salt is dissolved in the polar solvent. In certain embodiments, the reactions conditions include holding the reaction mixture at between about room temperature and about 80° C. for between about 1 hour and about 20 hours such that at least about 50% yield is obtained.
Three-Component Reactions of Arynes, Amines, and Nucleophiles via a One-Pot Process
Min, Gyoungwook,Seo, Jeongseob,Ko, Haye Min
, p. 8417 - 8425 (2018/07/15)
An unprecedented three-component reaction of arynes, tertiary amines, and nucleophiles has been demonstrated through ammonium salt intermediates. This protocol allows access to tertiary aniline derivatives containing the piperazine motif in good-to-excell
Ortho vs ipso: Site-selective pd and norbornene-catalyzed arene c-h amination using aryl halides
Dong, Zhe,Dong, Guangbin
supporting information, p. 18350 - 18353 (2014/01/06)
A Pd and norbornene-catalyzed ortho-arene amination via Catellani-type C-H functionalization is reported. Aryl halides are used as substrates; N-benzoyloxyamines and isopropanol are employed as the amine source (oxidant) and reductant respectively. Exampl
Rapid and convenient synthesis of N-arylmorpholines under microwave irradiation
Li, Hong Bo,Liang, Wu,Ma, Chang Peng,Kai, Yong Mao,Li, Lei,Zhang, Yong Gang
, p. 995 - 998 (2013/08/23)
A series of N-arylmorpholines 1a-1n was obtained by cyclocondensation of arylamines and diethylene glycol dimesylate under microwave irradiation in an aqueous potassium carbonate medium. The reaction is rapid and convenient, and a variety of functional groups are tolerated in the process.
Transition-metal-free electrophilic amination of arylboroxines
Xiao, Qing,Tian, Leiming,Tan, Renchang,Xia, Ying,Qiu, Di,Zhang, Yan,Wang, Jianbo
experimental part, p. 4230 - 4233 (2012/09/22)
A transition-metal-free strategy to construct C(sp2)-N bonds using arylboroxines and O-benzoyl hydroxylamines as coupling partners has been developed. This transformation provides a useful method to access various aromatic amines.
Manganese-catalyzed cross-coupling reactions of aliphatic amines with aryl halides
Yong, Fui-Fong,Teo, Yong-Chua
supporting information; experimental part, p. 3910 - 3912 (2010/08/20)
An efficient and convenient protocol has been developed for the N-arylation of aliphatic amines with differently substituted aryl halides using a MnCl2·4H2O/l-proline catalyst and NaOt-Bu as the base in DMSO.
Efficient iron-catalyzed N-arylation of aryl halides with amines
Quo, Diliang,Huang, He,Xu, Jinyi,Jiang, Hualiang,Liu, Hong
supporting information; scheme or table, p. 4513 - 4516 (2009/05/07)
(Chemical Equation Presented) A practical and promising protocol was developed for N-arylations of various amines with differently substituted aryl halides. The processes are efficiently promoted by the catalyst system involving the environmentally benign Fe2O3 and the universal ligand L-proline. The versatility, convenient operation, low cost, and environmental friendliness, in combination with the high yields, render this method viable for use in both laboratory research and larger industrial scales.
