1007120-38-8Relevant academic research and scientific papers
Sonogashira Cross-Coupling of Aryltrimethylammonium Salts
Chen, Qianwei,Gao, Fengchen,Tang, Huiling,Yao, Miao,Zhao, Qian,Shi, Yanhui,Dang, Yanfeng,Cao, Changsheng
, p. 3730 - 3736 (2019)
A protocol for C(sp)-C(sp2) bond formation via the Sonogashira coupling reaction involving C-N bond cleavage with aryltrimethylammonium triflate as an electrophilic coupling partner is described in this work. The reactions proceeded well under mild conditions with a stoichiometric ratio of alkyl, aryl, or heteroaryl acetylenes and provided yields of up to 93%. Numerous useful functional groups were tolerated under the reaction conditions. Direct amine alkynylation can be achieved through a one-pot process without the isolation of ammonium salt. The protocol can be performed on a gram scale. Density functional theory calculations were performed to investigate the reaction mechanism that involved oxidative addition, alkyne coordination, deprotonation, and reductive elimination, which yielded the cross-coupling product.
LiHMDS-Promoted Palladium-Catalyzed Sonogashira Cross-Coupling of Aryl Fluorides with Terminal Alkynes
He, Jingjing,Yang, Kang,Zhao, Jianhong,Cao, Song
, p. 9714 - 9718 (2019)
A highly efficient Pd-catalyzed Sonogashira coupling of various aryl fluorides with terminal alkynes in the presence of LiHMDS was developed. Both unreactive electron-rich fluoroarenes and electron-poor fluoroarenes proceeded smoothly and afforded the cor
Gold-Catalyzed Dimerization of Diarylalkynes: Direct Access to Azulenes
Claus, Vanessa,Schukin, Michael,Harrer, Siegfried,Rudolph, Matthias,Rominger, Frank,Asiri, Abdullah M.,Xie, Jin,Hashmi, A. Stephen K.
, p. 12966 - 12970 (2018)
We have developed a simple gold-catalyzed procedure for the synthesis of substituted and modifiable azulenes. The azulenes are formed either by the dimerization of push–pull diarylalkynes bearing a fluorine atom in ortho or para position or by the dimeriz
Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling
Valishina, Elena A.,Silva, M.Fátima C. Guedes Da,Kinzhalov, Mikhail A.,Timofeeva, Svetlana A.,Buslaeva, Tatyana M.,Haukka, Matti,Pombeiro, Armando J.L.,Boyarskiy, Vadim P.,Kukushkin, Vadim Yu.,Luzyanin, Konstantin V.
, p. 162 - 171 (2014)
The metal-mediated coupling between cis-[PdCl2(CNR 1)2] [R1 = cyclohexyl (Cy) 1, t-Bu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC 6H3 4] and hydrazones H2
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.
Application of palladium complexes bearing acyclic amino(hydrazido)carbene ligands as catalysts for copper-free Sonogashira cross-coupling
Timofeeva, Svetlana A.,Kinzhalov, Mikhail A.,Valishina, Elena A.,Luzyanin, Konstantin V.,Boyarskiy, Vadim P.,Buslaeva, Tatyana M.,Haukka, Matti,Kukushkin, Vadim Yu.
, p. 449 - 456 (2015/07/15)
Abstract Metal-mediated coupling of one isocyanide in cis-[PdCl2(CNR1)2] (R1 = C6H11 (Cy) 1, tBu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3
Ethynyl-cyclohexanol: an efficient acetylene surrogate in Sonogashira coupling
Csékei, Márton,Novák, Zoltán,Kotschy, András
, p. 975 - 982 (2008/09/17)
The Sonogashira coupling of aryl halides in the presence of 1-ethynyl-cyclohexanol as an acetylene source provides an efficient method for the synthesis of diarylacetylenes without the isolation of the appropriate arylacetylenes.
