157366-46-6Relevant articles and documents
New air-stable planar chiral ferrocenyl monophosphine ligands: Suzuki cross-coupling of aryl chlorides and bromides
Jensen, Jakob F.,Johannsen, Mogens
, p. 3025 - 3028 (2003)
(Matrix presented) A novel class of planar chiral electron-rich monophosphine ligands has been developed. The modular design allows a short and efficient synthesis of an array of aryl-ferrocenyl derivatives carrying the donating bis(dicyclohexyl)phosphino moiety. These new ligands have successfully been applied in the palladium-catalyzed Suzuki cross-coupling of activated as well as nonactivated aryl chlorides at room temperature. The asymmetric coupling of an aryl bromide and an aryl boronic acid was also tested, giving ees up to 54%.
Cu-Catalyzed Denitrogenative Ring-Opening of 3-Aminoindazoles for the Synthesis of Aromatic Nitrile-Containing (Hetero)Arenes
Zhou, Yao,Deng, Shuilin,Mai, Shaoyu,Song, Qiuling
supporting information, p. 6161 - 6165 (2018/10/05)
An unprecedented Cu-catalyzed oxidative cleavage of two C-N bonds of 3-aminoindazoles is reported herein, which represents the first example for denitrogenative ring-opening of 3-aminoindazoles. This novel reactivity of 3-aminoindazoles enables the produc
The Rational Design and Synthesis of Water-Soluble Thiourea Ligands for Recoverable Pd-Catalyzed Aerobic Aqueous Suzuki-Miyaura Reactions at Room Temperature
Chen, Wei,Lu, Xiao-Yan,Xu, Bei-Hua,Yu, Wei-Guo,Zhou, Zi-Niu,Hu, Ying
, p. 1499 - 1510 (2018/01/17)
Eight precatalysts containing carboxylic-functionalized thiourea ligands are prepared and their activities and recyclability are evaluated in aerobic aqueous Suzuki-Miyaura reactions. A bulky monothiourea-Pd complex, functionalized with four carboxylic groups, shows the best activity and recyclability in the coupling of aryl bromides with arylboronic acids. The catalyst can be reused at least five times without any significant reduction in its catalytic activity. TEM analysis and the confirmed catalytic activity of the observed black precipitate reveal that Pd nanoparticles are formed during the reactions and are stabilized by the carboxylic-functionalized thiourea ligands.
A simple and mild Suzuki reaction protocol using triethylamine as base and solvent
Li, Xinmin,Zhang, Hang,Hu, Qinghong,Jiang, Bo,Zeli, Yuan
supporting information, p. 3123 - 3132 (2018/12/04)
A simple and mild protocol for the palladium-catalyzed Suzuki reaction of aryl bromides and arylboronic acids is developed. The cross-coupling reactions can be performed at room temperature using 5.0 equiv. of Et3N as solvent and base without any ligands, and affording biaryl products in good yields. In addition, the chemoselecitive Suzuki reaction of bromo-N-methyliminodiacetic acid (MIDA) boronates with arylboronic acids can be achieved in this system, and various unsymmetrical terphenyls have been prepared in moderate yields by one-pot double Suzuki reactions.
Ruthenium-catalyzed hydrogenation of carbocyclic aromatic amines: Access to chiral exocyclic amines
Yan, Zhong,Xie, Huan-Ping,Shen, Hong-Qiang,Zhou, Yong-Gui
supporting information, p. 1094 - 1097 (2018/02/23)
The first highly enantioselective hydrogenation of carbocyclic aromatic amines has been successfully realized using in situ-generated chiral ruthenium complex as catalyst, affording facile access to chiral exocyclic amines with up to 98% ee.
An N-Heterocyclic Carbene-Nickel Half-Sandwich Complex as a Precatalyst for Suzuki-Miyaura Coupling of Aryl/Heteroaryl Halides with Aryl/Heteroarylboronic Acids
Ando, Shin,Matsunaga, Hirofumi,Ishizuka, Tadao
, p. 1266 - 1272 (2018/06/18)
A nickel half-sandwich complex supported by our original NHC ligand was developed as a robust precatalyst for Suzuki-Miyaura cross-coupling. The addition of PPh3 was a crucial element in the suppression of side reactions and in accelerating the cross-coupling reaction. By employing the optimal conditions, aryl-aryl, heteroaryl-aryl, and heteroaryl-heteroaryl couplings were achieved.
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.
In situ-generated nano-palladium-catalyzed ligand-free Suzuki-Miyaura reaction of potassium aryltrifluoroborates at room temperature
Liu, Chun,Li, Xinmin,Gao, Zhanming,Wang, Xinnan,Jin, Zilin
supporting information, p. 3954 - 3959 (2015/06/02)
A mild and simple protocol is described for the palladium-catalyzed ligand-free Suzuki-Miyaura reaction of potassium aryltrifluoroborates in aqueous ethanol at room temperature. Palladium nanoparticles are generated in situ in the reaction and demonstrate high activity towards a wide range of aryl bromides and potassium aryltrifluoroborates, providing biphenyls in good to excellent yields. Interestingly, only 1 equiv of K2CO3 is used in this catalytic system. Moreover, the key biaryl intermediate of 2-cyano-4′-methylbiphenyl within valsartan is prepared in a 95% yield after 2 h.
Water-soluble salen-Pd complex as an efficient catalyst for Suzuki-Miyaura reaction of sterically hindered substrates in pure water
Liu, Ya-Shuai,Gu, Ning-Ning,Liu, Ping,Ma, Xiao-Wei,Liu, Yan,Xie, Jian-Wei,Dai, Bin
supporting information, p. 7985 - 7989 (2015/12/31)
Water-soluble 2N2O-salen ligands and their palladium complexes were synthesized and used as efficient catalysts for the Suzuki-Miyaura reactions in pure water. Notably, the reactions of substrates with sterically demanding ortho substituents (aryl bromides and/or arylboronic acids) proceed smoothly to generate corresponding products with moderate to high yields using 0.5 mol % (salph)Pd (salph=N,N′-bis(4-SO3Na-salicylidene)-1,2-phenylenediamine) as the catalyst. Importantly, the catalytic system has the wide substrate scope and the high tolerance to various functional groups, including cyano, amino, nitro, methoxy, and acetyl. Moreover, the biaryl compounds were also obtained on a multi-gram scale by simple recrystallization with the system in the absence of any organic solvent, surfactant, or phase transfer agent and the catalyst was reused directly for the next cycle. Particularly, this protocol can be applied to synthesize aryl-substituted carbazolyl compounds.
Zwitterionic palladium complexes: Room-temperature Suzuki-Miyaura cross-coupling of sterically hindered substrates in an aqueous medium
Lee, Jhen-Yi,Ghosh, Dabalina,Lee, Jing-Yi,Wu, Shih-Sheng,Hu, Ching-Han,Liu, Shuang-De,Lee, Hon Man
, p. 6481 - 6492 (2015/02/19)
A series of new imidazolium chlorides were straightforwardly prepared from the reactions between chloroacetone and imidazole derivatives. Deprotonation of the methylene proton next to the ketone group in these salts by pyridine led to the formation of a monodentate ligand that coordinated to palladium, readily forming zwitterionic anionic palladium pyridine complexes bearing a formal positive charge on the ligand ancillary. The pyridine ligand in the zwitterionic complexes can be facilely replaced by phosphine ligands. Seven of these new complexes were successfully characterized by X-ray crystallography. The zwitterionic phosphine complexes were highly efficient in catalyzing room-temperature Suzuki-Miyaura reactions between sterically hindered aryl chlorides and arylboronic acids in an aqueous medium.
