10531-80-3Relevant articles and documents
Synthesis of isocyanides by reacting primary amines with difluorocarbene
Si, Yi-Xin,Zhu, Peng-Fei,Zhang, Song-Lin
supporting information, p. 9086 - 9090 (2020/11/30)
A general, convenient, and friendly route for preparing a versatile building block of isocyanides from primary amines is developed. Difluorocarbene, generated in situ from decarboxylation of chlorodifluoroacetate, reacts efficiently with primary amines to produce isocyanides. Various primary amines are well tolerated, including aryl, heteroaryl, benzyl, and alkyl amines, as well as amine residues in amino acids and peptides. Late-stage functionalization of biologically active amines is demonstrated, showing its practical capacity in drug design and peptide modification.
Application of chlorodifluoromethane as C1 source for synthesis of amidine compounds
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Paragraph 0048-0049, (2019/09/17)
The invention discloses an application of chlorodifluoromethane as a C1 source for synthesis of amidine compounds. Chlorodifluoromethane can be subjected to quadrupole bond cracking under a mild condition, and valuable amidine compounds can be obtained. Water and a solvent are added in the presence of chlorodifluoromethane, the chlorodifluoromethane can be efficiently cracked into a C1 synthon, and synthesis of the amidine compounds can be realized. The synthesis method uses no transition metal, has the characteristic of being environmentally friendly, is simple to operate and can obtain the amidine compounds by one step.
Cobalt-catalyzed synthesis of N-containing heterocycles: Via cyclization of ortho -substituted anilines with CO2/H2
Ke, Zhengang,Yu, Bo,Wang, Huan,Xiang, Junfeng,Han, Juanjuan,Wu, Yunyan,Liu, Zhenghui,Yang, Peng,Liu, Zhimin
, p. 1695 - 1701 (2019/04/10)
The CO2-involved synthesis of chemicals is of great significance from the green and sustainable chemistry viewpoint. Herein, we report a non-noble metal catalytic system composed of CoF2, CsF and P(CH2CH2PPh2)3 (denoted as PP3) for the synthesis of N-containing heterocycles from ortho-substituted anilines and CO2/H2. Mechanism investigation indicates that [Co(PP3)H(CO2)]+ is a catalytically active intermediate under working conditions; and CsF plays important roles in activating ortho-substituted anilines via hydrogen bond interactions, thus promoting the formation of the final products. This catalytic system is highly efficient, and allows a wide scope of ortho-substituted anilines, together with excellent functional group tolerance, affording various N-containing heterocycles in good to excellent yields.
Method for synthesizing benzoxazole through microwave radiation of benzamide compound in water phase
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Paragraph 0077, (2019/03/08)
The invention discloses a method for synthesizing benzoxazole through microwave radiation of a benzamide compound in a water phase. The benzamide compound is added into the water phase under the microwave condition to be subjected to a cyclization reaction for generating the benzoxazole under the alkali condition, and the method for preparing the benzoxazole is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applied to a large number of functional groups, the yield is high, the number of by-products is small, and the method is easy to operate, safe, low in cost and environmentally friendly. (Please see the specifications for the formula).
N-Substituted Formamides as C1-Sources for the Synthesis of Benzimidazole and Benzothiazole Derivatives by Using Zinc Catalysts
Nale, Deepak B.,Bhanage, Bhalchandra M.
, p. 2835 - 2842 (2015/12/18)
An efficient and convenient one-pot protocol has been developed for the synthesis of a variety of benzimidazole, benzoxazole, and benzothiazole derivatives. This novel approach uses various o-phenylenediamines and N-substituted formamides (C1 sources) in a zinc-catalyzed cyclization in the presence of poly(methylhydrosiloxane) to afford the corresponding derivatives as sole products in moderate to excellent yields.
Direct C-H iodination of 1,3-azoles catalysed by CuBr2
Zhao, Xia,Ding, Fang,Li, Jingyu,Lu, Kui,Lu, Xiaoyu,Wang, Bin,Yu, Peng
supporting information, p. 511 - 513 (2015/02/19)
A mild method was developed for the direct C-H iodination of 1,3-azoles catalysed by CuBr2. Compared with the traditional metalation/iodination sequences carried out with nBuLi or TMPLi (TMP = 2,2,6,6-tetramethylpiperidino), a relatively weaker base, LiOtBu, was used in the presence of 1,10-phenanthroline. Five series of 1,3-azoles, including benzoxazole, benzothiozole, N-methyl-benzoimidazole, 5-phenyloxazole and 2-phenyl-1,3,4-oxadiazole were tested and afforded the corresponding iodination products.
Palladium-catalyzed coupling of polyfluorinated arenes with heteroarenes via C-F/C-H activation
Yu, Daohong,Lu, Long,Shen, Qilong
supporting information, p. 940 - 943 (2013/03/29)
The first palladium-catalyzed coupling of 2-pyridyl-polyfluoroarenes and benzoxazole, thiazole, benzothiazole, benzoimidazole, oxazole or oxadiazole via a concurrent C-F/C-H activation is described. Initial mechanistic studies showed that C-F activation o
Direct arylation of benzoxazole C-H bonds with iodobenzene diacetates
Yu, Peng,Zhang, Guangyou,Chen, Fan,Cheng, Jiang
supporting information; experimental part, p. 4588 - 4590 (2012/09/22)
A Pd (OAc)2-catalyzed direct arylation of benzoxazole C-H bonds has been achieved with iodobenzene diacetates as the arylation reagent in moderate to good yields. The procedure tolerates a series of functional groups, such as methoxy, nitro, cyano, chloro, and bromo groups.
Palladium-catalyzed direct phosphonation of azoles with dialkyl phosphites
Hou, Chaodong,Ren, Yunlai,Lang, Rui,Hu, Xiaoxue,Xia, Chungu,Li, Fuwei
supporting information; experimental part, p. 5181 - 5183 (2012/06/01)
The first Pd-catalyzed direct phosphonation of azoles with dialkyl phosphites has been achieved without addition of base or acid. This method involves the oxidative cleavage of C-H and P(O)-H bonds and represents an atom-efficiency alternative to the classical phosphonation of Ar-X. A Pd II/PdIV mechanism has been studied and proposed.
Copper-catalyzed oxidative amination of benzoxazoles via C-H and C-N bond activation: A new strategy for using tertiary amines as nitrogen group sources
Guo, Shengmei,Qian, Bo,Xie, Yinjun,Xia, Chungu,Huang, Hanmin
experimental part, p. 522 - 525 (2011/04/18)
An efficient and conceptually new method for oxidative amination of azoles with tertiary amines via copper-catalyzed C-H and C-N bond activation has been developed. This protocol can be performed in the absence of external base and only requires atmospheric oxygen as oxidant. The catalyst system is very simple and efficient, which opens a new way for using tertiary amines as nitrogen group sources for C-N bond formation reactions.
