1034142-69-2Relevant academic research and scientific papers
Atom-Economical Thiocyanation-Amination of Alkynes with N-Thiocyanato-Dibenzenesulfonimide
Wu, Haopeng,Shao, Chukai,Wu, Di,Jiang, Liang,Yin, Hongquan,Chen, Fu-Xue
, p. 5327 - 5335 (2021/04/06)
A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by N-thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C-S bond and C-N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.
Synthesis, crystal structures, and application of two new pincer type palladium(II)-Schiff base complexes in C-C cross-coupling reactions
Agrahari, Bhumika,Layek, Samaresh,Anuradha,Ganguly, Rakesh,Pathak, Devendra D.
, p. 345 - 354 (2017/12/01)
Two new pincer type Pd(II)-Schiff base complexes of the general formula [PdL1(PPh3)] 1 and [PdL2(PPh3)] 2, (where L1 = 2-(2,3-Dihydroxybenzylideneamino)phenolate and L2 = 2-(2,3-dihydroxybenzylidene)hydrazinecarbothioamidate) were synthesised by the reaction of the palladium acetate with the corresponding ligand in methanol as yellow crystalline solids in high yields. Both complexes were fully characterized by FT-IR, 1H NMR, 13C NMR, 31P NMR, elemental analysis and single crystal X-ray diffraction studies. The crystal structures confirmed the tridentate nature of the pincer type Schiff base ligands and the distorted square planar geometry around the metal centre in both cases. The triphenylphosphine acted as an auxiliary ligand and occupied the fourth coordination site at palladium. The complexes were found to be efficient homogenous catalysts for a series of Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions at a low catalyst loading (0.08 mol%), and without the use of any additives. All organic products were fully characterized by 1H and 13C NMR studies.
Sonogashira-type cross-coupling reactions catalyzed by copper complexes of pincer N-heterocyclic carbenes
Domyati, Doaa,Latifi, Reza,Tahsini, Laleh
supporting information, p. 98 - 105 (2018/03/06)
Copper complexes of N-heterocyclic carbenes (NHC) have recently received great attention in catalysis, however, the application scope has been limited to neutral complexes bearing monodentate ligands. Herein, we report the synthesis and full characterization of a cationic Cu-pincer bis(NHC) complex with bulky tert-butyl wingtips that serves as catalyst for the coupling of aryl iodides and phenylacetylene, alongside its analogs with small alkyl substituents. Unlike other copper catalysts that require an inert atmosphere to prevent alkyne homocoupling, a competing side reaction to Sonogashira reaction, the Cu-pincer bis(NHC) complexes provide good to excellent cross-coupling yields in air. Interestingly, the reaction under argon affords substantially reduced cross-coupling, indicative of the oxygen involvement and its facilitating effect in the mechanism. In our controlled studies, the air-assisted cross-coupling reaction came to a complete stop when using a radical trap, suggesting the presence of a radical in the mechanism. Examining the reaction of Cu-pincer bis(NHC) complexes with oxygen via UV–vis spectroscopy reveals a dark green chromophore formation at ?40 °C with strong absorbance (ε > 400 M?1cm?1) at 460 nm and 500 nm, likely due to a high-valent copper-oxygen adduct.
Sonogashira reaction using arylsulfonium salts as cross-coupling partners
Tian, Ze-Yu,Wang, Shi-Meng,Jia, Su-Jiao,Song, Hai-Xia,Zhang, Cheng-Pan
, p. 5454 - 5457 (2017/11/06)
Triarylsulfonium, alkyl- and fluoroalkyl(diaryl)-sulfonium, and aryl(dialkyl)sulfonium triflates are successfully used as a new family of cross-coupling participants in the Sonogashira reaction as aryldiazonium, diaryliodonium, and tetraphenylphosphonium salts. It was found that terminal alkynes reacted mildly with triarylsulfonium or (2,2,2-trifluoroethyl)diphenylsulfonium triflate at room temperature under Pdand Cu-cocatalysis to give the corresponding arylalkynes in up to >99% yield. This protocol represents the first use of arylsulfonium salts as cross-coupling partners in the Pd/Cu-catalyzed Sonogashira reaction.
Chemoselective synthesis of unsymmetrical internal alkynes or vinyl sulfones via palladium-catalyzed cross-coupling reaction of sodium sulfinates with alkynes
Xu, Yanli,Zhao, Jinwu,Tang, Xiaodong,Wu, Wanqing,Jiang, Huanfeng
, p. 2029 - 2039 (2014/07/07)
A highly efficient and mild palladium-catalyzed cross-coupling of sodium sulfinates and alkynes for the selective synthesis of unsymmetrical internal alkynes and vinyl sulfones has been developed. This methodology has advantages of easily accessible starting materials, functional group tolerance and a wide range of substrates, which provides rapid access to alkynes and vinyl sulfones.
An alternative role for acetylenes: Activation of fluorobenzenes toward nucleophilic aromatic substitution
Bizier, Nicholas P.,Wackerly, Jay Wm.,Braunstein, Eric D.,Zhang, Mengfei,Nodder, Stephen T.,Carlin, Stephen M.,Katz, Jeffrey L.
, p. 5987 - 5998 (2013/07/26)
Acetylenes are increasingly versatile functional groups for a range of complexity-building organic transformations and for the construction of desirable molecular architectures. Herein we disclose a previously underappreciated aspect of arylacetylene reac
