1007120-38-8Relevant articles and documents
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.
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
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.
