26170-92-3Relevant academic research and scientific papers
Transient-Ligand-Enabled ortho-Arylation of Five-Membered Heterocycles: Facile Access to Mechanochromic Materials
Li, Bijin,Seth, Kapileswar,Niu, Ben,Pan, Lei,Yang, Huiwen,Ge, Haibo
supporting information, p. 3401 - 3405 (2018/02/28)
Reported herein is the first example of a direct arylation of heteroarenes by a transient-ligand-directed strategy without the need to construct and deconstruct the directing group. A wide range of heteroarenes undergoes the coupling with diverse aryl iod
Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates
Zhang, Enxuan,Tang, Jiaze,Li, Suhua,Wu, Peng,Moses, John E.,Sharpless, K. Barry
supporting information, p. 5692 - 5697 (2016/04/20)
A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 gas. These substrates are highly efficient coupling partners in the Suzuki reaction. Through judicious selection of Pd catalysts the fluorosulfate functionality is differentiated from bromide and chloride; the order of reactivity being: -Br> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib. A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 gas. These substrates are highly efficient coupling partners in the Suzuki reaction. Through judicious selection of Pd catalysts the fluorosulfate functionality is differentiated from bromide and chloride; the order of reactivity being: -Br> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.
Iron-Catalyzed arylation of heterocycles via directed c-h bond activation
Sirois, John J.,Davis, Riley,Deboef, Brenton
supporting information, p. 868 - 871 (2014/03/21)
The iron-catalyzed arylation of aromatic heterocycles, such as pyridines, thiophenes, and furans, has been achieved. The use of an imine directing group allowed for the ortho functionalization of these heterocycles with complete conversion in 15 min at 0
Palladacycle-catalyzed Suzuki-Miyaura reaction of aryl/heteroaryl halides with MIDA boronates in EtOH/H2O or H2O
Li, Yabo,Wang, Jingran,Wang, Zhiwei,Huang, Mengmeng,Yan, Beiqi,Cui, Xiuling,Wu, Yusheng,Wu, Yangjie
, p. 36262 - 36266 (2014/11/08)
With good to excellent yields, a series of mono- or diheteroaryl compounds were synthesized via the palladacycle-catalyzed Suzuki-Miyaura reaction of various N-methyliminodiacetic acid (MIDA) boronates with aryl/heteroaryl halides in EtOH/H2O or H2O. This journal is the Partner Organisations 2014.
Direct C-H arylation of thiophenes at low catalyst loading of a phosphine-free bis(alkoxo)palladium complex
Li, Yabo,Wang, Jingran,Huang, Mengmeng,Wang, Zhiwei,Wu, Yusheng,Wu, Yangjie
, p. 2890 - 2897 (2014/05/06)
An efficient phosphine-free direct C-H arylation of thiophenes at the α-position has been developed at low catalyst loading of bis(alkoxo)palladium complex (Cat.I, 0.1-0.2 mol %). The developed synthetic method can be applied to the synthesis of α-aryl/heteroaryl thiophenes from aryl or heteroaryl bromides in good to excellent yields and is compatible with the substrates bearing electron-donating or electron-withdrawing groups. The reactivities of the 2- and 5-positions of thiophenes are equivalent and not dependent on steric hindrance under optimal conditions. This condition can also be applied to other heterocyclic moieties such as benzothiophene, benzofuran, and pyrrole with high conversion yields.
Regioselective Synthesis of 2-Functionalized Thiophenes by Condensation of α-Mercapto Compounds with β-Aminoenone Derivatives
Alberola, Angel,Andres, Jose M.,Gonzalez, Alfonso,Pedrosa, Rafael,Pradanos, Pedro
, p. 2537 - 2547 (2007/10/02)
2-Acylthiophenes and ethyl 2-thiophenecarboxylates are prepared regioselectively by reaction of 3-chloroenones and 2-acylenammonium chlorides with α-mercapto derivatives in good to moderate yields.
