1204-43-9Relevant academic research and scientific papers
Readily available catalysts for demanding Suzuki–Miyaura couplings under mild conditions
Demchuk, Oleg M.,Kap?on, Katarzyna,Mazur, Liliana,Strzelecka, Dorota,Pietrusiewicz, K. Micha?
, p. 6668 - 6677 (2016)
A straightforward synthesis of a sterically hindered and electron rich bidentate monophosphine biaryl ligand Sym-Phos of C,P-type of complexation was realised in a high yield starting from simple substrates in easily affordable conditions. In combination with a palladium source, the obtained ligand formed a highly active catalyst mediating sterically demanding Suzuki–Miyaura coupling reactions in aqueous media even at 60 °C and with no need to protect the reaction mixture by an inert gas.
Ruthenium-Catalyzed Enantioselective Hydrogenation of Phenanthridine Derivatives
Yang, Zhusheng,Chen, Fei,Zhang, Shuxin,He, Yanmei,Yang, Nianfa,Fan, Qing-Hua
, p. 1458 - 1461 (2017)
The first asymmetric hydrogenation of phenanthridines catalyzed by chiral cationic ruthenium diamine complexes has been developed with up to 92% ee and full conversions. The choice of the counteranion of the catalyst was found to be critical for achieving high enantioselectivity. In addition, the obtained 5,6-dihydrophenanthridine could be used as a chiral hydride donor for organocatalytic asymmetric transfer hydrogenation.
Photo-Driven Synthesis of C6-Polyfunctionalized Phenanthridines from Three-Component Reactions of Isocyanides, Alkynes, and Sulfinic Acids by Electron Donor-Acceptor Complex
Li, Yang,Miao, Tao,Li, Pinhua,Wang, Lei
, p. 1735 - 1739 (2018)
A novel and efficient photoinduced synthesis of C6-polyfunctionalized phenanthridines from three-component reactions of isocyanides, alkynes and sulfinic acids was developed. The reactions generated the corresponding products with high selectivity through
Synthesis of [14C]KT3-671, 2-propyl-8-oxo-1-[(2'-(1H- [14C] tetrazole-5-yl) biphenyl-4-yl) methyl]-4,5,6,7- tetrahydro-cycloheptimidazole, a novel potent nonpeptide angiotensin II receptor antagonist
Ueyama,Yanagisawa,Tomiyama
, p. 915 - 919 (1995)
2-Propyl-8-oxo-1-[(2'-(1H-tetrazole-5-yl)biphenyl-4-yl) methyl]4,5,6,7-tetrahydrocyclohept imidazole (KT3-671), which has been found to be a potent and selective angiotesin II receptor antagonist, was synthesized in 14C-labelled form by using potassium[14C]-cyanide. [14C](KT3-671) 9 with a specific activity of 1.74GBq/mmol was prepared in four steps in 29.8% overall radiochemical yield from potassium[14C]-cyanide.
Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines
Gillespie, James E.,Morrill, Charlotte,Phipps, Robert J.
supporting information, p. 9355 - 9360 (2021/07/19)
The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.
Modular Tandem Mizoroki-Heck/Reductive Heck Reactions to Construct Fluorenes from Cyclic Diaryliodoniums
Peng, Xiaopeng,Yang, Yang,Luo, Bingling,Wen, Shijun,Huang, Peng
supporting information, p. 222 - 226 (2020/12/01)
Starting from cyclic diaryliodoniums and terminal alkenes, a diverse set of fluorenes is conveniently constructed. The reactions catalyzed by palladium undergo one conventional Mizoroki-Heck reaction and one reductive Heck reaction. The scope of alkenes is general, leading to 29 fluorenes which would expand the structural diversity of fluorene reservoir. (Figure presented.).
Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids
Zhou, Liwei,Sun, Mingjie,Zhou, Fengru,Deng, Guobo,Yang, Yuan,Liang, Yun
supporting information, p. 7150 - 7155 (2021/09/18)
A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.
Palladium-Catalyzed C-H Amination/[2 + 3] or [2 + 4] Cyclization via C(sp3or sp2)-H Activation
An, Yang,Ding, Ya-Nan,Gou, Xue-Ya,Li, Qiao,Li, Yuke,Liang, Yong-Min,Zhang, Xiao-Yan,Zhang, Zhe
supporting information, p. 7961 - 7965 (2021/10/25)
This report describes a palladium-catalyzed Catellani reaction consisting of amination/[2 + 3] or [2 + 4] cyclization via a carboxylate ligand-exchange strategy. This method effectively activates ortho-substituents that avoid a second C-H palladation. The scope of substrates was broad, o-methyl-substituted iodoarenes were applied to the reaction smoothly, and o-phenyl-substituted iodoarenes can also be obtained by this method. In terms of mechanism, density functional theory calculations proved the sequence of the key five-membered aryl-norbornene-palladacycle intermediate formation and C(sp3 or sp2)-H activation.
Synthesis of Fluorescent 4-Azapyrenes by Palladium(II)-Catalyzed Dual C?H Bond Activation and Annulation
Hsiao, Huan-Chang,Annamalai, Pratheepkumar,Jayakumar, Jayachandran,Sun, Shang-You,Chuang, Shih-Ching
supporting information, p. 1695 - 1701 (2021/02/12)
Unique dual-emissive and deep-blue/green fluorescent multi-substituted 4-azapyrenes with bathochromic shift emission, quantum yields up to 0.60 and long excited-state lifetime were synthesized successfully by annulative π-extension reactions. This synthesis constitutes a palladium-catalyzed dehydrogenative annulation of N-acyl-2-aminobiaryls with in situ 1,3-diynes as a key step, giving substituted phenanthrenes via a rollover C?H bond activation, followed by Bischler-Napieralski cyclization. Further π-extension by superacid-mediated cyclization produced a blue fluorescent naphtho 4-azapyrene. (Figure presented.).
4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics
Liu, Yan,Chen, Xiao-Lan,Li, Xiao-Yun,Zhu, Shan-Shan,Li, Shi-Jun,Song, Yan,Qu, Ling-Bo,Yu, Bing
supporting information, p. 964 - 972 (2021/01/12)
2,4,5,6-Tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile (4CzIPN-tBu) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-tBu as catalyst, we developed a visible-light-induced proton-coupled electron transfer strategy for the generation of phosphorus-centered radicals, via which a wide range of phosphorylated phenanthridines, quinolines, and benzothiazoles were successfully constructed.
