25775-03-5Relevant academic research and scientific papers
Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles
Edjoc, Racquel K.,Mills, L. Reginald,Rousseaux, Sophie A. L.
, p. 10422 - 10428 (2021/07/26)
The design of new ligands for cross-coupling is essential for developing new catalytic reactions that access valuable products such as pharmaceuticals. In this report, we exploit the reactivity of nitrile-containing additives in Ni catalysis to design a benzonitrile-containing ligand for cross-coupling involving tertiary nucleophiles. Kinetic and Hammett studies are used to elucidate the role of the optimized ligand, which demonstrate that the benzonitrile moiety acts as an electron-acceptor to promote reductive elimination over β-hydride elimination and stabilize low-valent Ni. With these conditions, a protocol for decyanation-metalation and Ni-catalyzed arylation is conducted, enabling access to quaternary α-arylnitriles from disubstituted malononitriles.
PYRAZOLYL COMPOUNDS AND METHODS OF USE THEREOF
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Paragraph 0312-0317, (2020/05/14)
Compounds having activity as chemotherapeutic agents are provided. The compounds have the following structure (I): or a pharmaceutically acceptable salt, stereoisomer, isotopic form or prodrug thereof, wherein R1a, R1b, R1c, R1d, L, and are as defined herein. Methods associated with preparation and use of such compounds, pharmaceutical compositions comprising such compounds and methods for treating cancer (e.g., hematological cancers) are also provided.
Rh(III)-Catalyzed C-H Cyanation of 2 H-Indazole with N-Cyano- N-phenyl- p-toluenesulfonamide
Li, Jing,Shi, Linlin,Zhang, Shu-Ping,Wang, Xu-Yan,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
, p. 10835 - 10845 (2020/09/18)
A Rh(III)-catalyzed direct cyanation of 2H-indazoles with N-cyano-N-phenyl-p-toluenesulfonamide has been realized via a chelation-assisted strategy. The methodology enables regioselective access to various ortho-cyanated phenylindazoles in good yields with a broad substrate scope and good functional group compatibility. The obtained cyanated indazoles could further be converted into other value-added chemicals. Importantly, the current protocol is featured with several characteristics, including a novel cyanating agent, good regioselectivity, and operational convenience.
Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation
Chen, Fengyang,Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Zhou, Qifan
, p. 4590 - 4600 (2019/12/11)
In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.
Rhodium(iii)-catalyzed aromatic C-H cyanation with dimethylmalononitrile as a cyanating agent
Li, He,Zhang, Sheng,Yu, Xiaoqiang,Feng, Xiujuan,Yamamoto, Yoshinori,Bao, Ming
supporting information, p. 1209 - 1212 (2019/01/30)
A rhodium-catalyzed aromatic C-H bond direct cyanation with safe, bench-stable, and commercially available dimethylmalononitrile as the cyanating agent has been successfully developed by using copper oxide as a promotor. Pyridine, quinoline, pyrimidine and pyrazole were used as the directing group in this type of C-H bond direct cyanation reaction.
Cu(II)-catalyzed C-N coupling of (hetero)aryl halides and N-Nucleophiles promoted by α-benzoin oxime
Yuan, Chunling,Zhang, Lei,Zhao, Yingdai
, (2019/11/28)
We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaαolds found in FDA-approved pharmaceuticals.
L -(-) -Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles
Zhou, Qifan,Du, Fangyu,Chen, Yuanguang,Fu, Yang,Sun, Wenjiao,Wu, Ying,Chen, Guoliang
, p. 8160 - 8167 (2019/06/28)
l-(-)-Quebrachitol (QCT) has been found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.
α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles
Yuan, Chunling,Zhao, Yingdai,Zheng, Li
, p. 2173 - 2180 (2019/11/25)
The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C-N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-Arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.
Rhodium-Catalyzed Direct C-H Bond Cyanation in Ionic Liquids
Lv, Songyang,Li, Yaling,Yao, Tian,Yu, Xinling,Zhang, Chen,Hai, Li,Wu, Yong
supporting information, p. 4994 - 4997 (2018/08/24)
A Cp?Rh(III)/IL-based direct C-H bond cyanation system was developed for the first time. The system is a mild, efficient, and recyclable method for the synthesis of aryl nitriles. Many different directing groups can be used in this cyanation, and the reaction tolerates a variety of functional groups.
α-Iminonitrile: A new cyanating agent for the palladium catalyzed C-H cyanation of arenes
Chen, Zhen-Bang,Zhang, Fang-Ling,Yuan, Qing,Chen, Hai-Fang,Zhu, Yong-Ming,Shen, Jing-Kang
, p. 64234 - 64238 (2016/07/23)
An efficient palladium-catalyzed C-H cyanation reaction of arenes using α-iminonitrile as a new cyanating reagent has been developed. With high regioselectivity and broad substrate scope, this reaction offers monocyanated products in moderate to excellent
