35070-08-7Relevant articles and documents
N-Heterocarbene Palladium Complexes with Dianisole Backbones: Synthesis, Structure, and Catalysis
Li, Dong-Hui,He, Xu-Xian,Xu, Chang,Huang, Fei-Dong,Liu, Ning,Shen, Dong-Sheng,Liu, Feng-Shou
, p. 2539 - 2552 (2019/06/17)
A series of palladium N-heterocyclic carbenes (NHCs), complexes C1-C5, bearing dianisole backbones and substituted N-aryl moieties have been synthesized and characterized. The electronic effect as well as the steric environment of the NHC ligands has been assessed. The synthesized palladium complexes were applied for Suzuki-Miyaura cross-coupling reactions under aerobic conditions. The relationship between the catalytic structure and catalytic performance was then extensively investigated. Upon optimizing the reaction conditions, the C4 was found to be highly efficient to catalyze the cross-coupling of (hetero)aryl chlorides with (hetero)arylboronic acids at a 0.1 mol % palladium loading.
Suzuki-Miyaura cross-coupling for efficient synthesis of aryl-substituted N-heteroarenes catalyzed by recyclable N-phenylpiperazine-Palladium(II) complex
Perumgani, Pullaiah C.,Kodicherla, Balaswamy,Mandapati, Mohan Rao,Parvathaneni, Sai Prathima
supporting information, p. 227 - 232 (2018/04/02)
Polystyrene supported N-phenylpiperazine-Pd(II) complex D was synthesized and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electronmicroscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and thermal analysis (TG-DTA). This heterogeneous Pd(II) complex showed high catalytic efficiency for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides, aryl chlorides to give the corresponding 2-arylpyridines and heteroarenes. The coupled products were formed in excellent yields at low catalyst loadings under mild reaction conditions. Further, this heterogeneous catalyst showed excellent recyclability and reused for four cycles with no significant decrease in its activity.
Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides
Duong, Hung A.,Wu, Wenqin,Teo, Yu-Yuan
supporting information, p. 4363 - 4366 (2017/12/05)
An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.
Insight into Copper Catalysis: In Situ Formed Nano Cu2O in Suzuki-Miyaura Cross-Coupling of Aryl/Indolyl Boronates
Ranjani, Ganapathy,Nagarajan, Rajagopal
, p. 3974 - 3977 (2017/08/14)
A ligand-free copper catalyzed Suzuki-Miyaura coupling of 3,5-diiodopyridine with aryl and indole boronates has been explored in good to excellent yields. In situ generation of nano-Cu2O from CuCl2 under the reaction conditions has been discovered for the first time. The generality of the reaction was further demonstrated by the arylation of 5-iodopyrimidine, iodopyridines, iodobenzenes, and diiodobenzenes and resulted in good to moderate yields. Moreover, bisindole alkaloid Scalaridine A has been successfully synthesized in 60% overall yield.
Pd-Catalyzed Ligand-Free Synthesis of Arylated Heteroaromatics by Coupling of N-Heteroaromatic Bromides with Iodobenzene Diacetate, Iodosobenzene, or Diphenyliodonium Salts
Wang, Xiajun,He, Yongqin,Ren, Mengdan,Liu, Shengkang,Liu, He,Huang, Guosheng
, p. 7958 - 7962 (2016/09/09)
An efficient method for synthesizing arylated heteroaromatics has been reported via Pd-catalyzed ligand-free cross-coupling of N-heteroaromatic bromides with iodine(III) reagents under mild conditions. Iodobenzene diacetate, iodosobenzene, and diphenyliod
Oxygen-promoted Pd/C-catalyzed Suzuki-Miyaura reaction of potassium aryltrifluoroborates
Liu, Chun,Liu, Chao,Li, Xin-Min,Gao, Zhan-Ming,Jin, Zi-Lin
, p. 631 - 634 (2016/05/19)
A simple and highly efficient protocol has been developed for the Pd/C-catalyzed ligand-free Suzuki-Miyaura reaction of potassium aryltrifluoroborates. In this catalytic system, the results demonstrate that oxygen plays a positive role in the cross-coupling reaction. In addition, this catalytic system could be successfully applied to synthesize biaryl compounds containing a carbazole moiety and the catalyst was recycled seven times without significant loss of catalytic activity.
A General Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl and Heteroaryl Chlorides
Yuen, On Ying,So, Chau Ming,Man, Ho Wing,Kwong, Fuk Yee
supporting information, p. 6471 - 6476 (2016/05/09)
A general palladium-catalyzed Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryl and heteroaryl trialkoxysilanes by a Pd(OAc)2/L2 catalytic system is presented. A newly developed water addition protocol can dramatically improve the product yields. The conjugation of the Pd/L2 system and the water addition protocol can efficiently catalyze a broad range of electron-rich, -neutral, -deficient, and sterically hindered aryl chlorides and heteroaryl chlorides with excellent yields within three hours and the catalyst loading can be down to 0.05 mol % Pd for the first time. Hiyama coupling of heteroaryl chlorides with heteroaryl silanes is also reported for the first time. The reaction can be easily scaled up 200 times (100 mmol) without any degasification and purification of reactants; this facilitates the practical application in routine synthesis.
Supporting ligand-assisted N-heterocyclic carbene palladium complexes: Characterization, computation, and catalytic activity in Suzuki-Miyaura cross coupling between aryl and heteroaromatic chlorides and various boronic acids
Shen, An,Hu, Yu-Cai,Liu, Ting-Ting,Ni, Chen,Luo, Yong,Cao, Yu-Cai
supporting information, p. 2055 - 2058 (2016/04/26)
A new series of imine-Pd-(N-heterocyclic carbene) complexes have been developed as efficient catalysts for Pd-catalyzed Suzuki-Miyaura coupling reaction. Based on the performance of supporting ligands, correlation of structure and catalytic activity has been demonstrated via experimental and computational modeling. A broad reaction scope of aryl and heteroaromatic chlorides could proceed at extremely low catalyst loading (minimum 0.005 mol %).
Palladium-catalyzed ligand-free and efficient Suzuki-Miyaura reaction of N-methyliminodiacetic acid boronates in water
Liu, Chun,Li, Xinmin,Wang, Xinnan,Qiu, Jieshan
, p. 1208 - 1215 (2016/03/01)
A green and efficient protocol has been developed for the Pd(OAc)2-catalyzed ligand-free Suzuki-Miyaura reaction of N-methyliminodiacetic acid (MIDA) boronates in water. In the presence of Pd(OAc)2 as a catalyst and (i-Pr)2NH as a base, the cross-coupling reactions of aryl bromides with aryl MIDA boronates proceeded smoothly in water without any surfactant, and various functional groups were tolerated under the optimized conditions.
Iron catalyzed oxidative assembly of N-heteroaryl and aryl metal reagents using oxygen as an oxidant
Liu, Kun Ming,Liao, Lian Yan,Duan, Xin Fang
supporting information, p. 1124 - 1127 (2015/01/09)
An equivalent amount of N-heteroaryl and aryl Grignard or lithium reagents, after mediation by an equivalent of titanate, was facilely coupled to furnish N-heteroaryl-aryl compounds under the catalysis of FeCl3/TMEDA at ambient temperature using oxygen as an oxidant. Most of the common N-heteroaryls were all good candidates, and thus provided a general, green and pratical protocol for the flexible construction of various N-heteroaryl-aryl structures. This journal is
