87639-43-8Relevant articles and documents
External Oxidant-Free Oxidative Tandem Cyclization: NaI-Catalyzed Thiolation for the Synthesis of 3-Thiosubstituted Pyrroles
Yuan, Bingxiang,Jiang, Yong,Qi, Zhenjie,Guan, Xin,Wang, Ting,Yan, Rulong
supporting information, p. 5112 - 5117 (2019/11/11)
A simple method for the synthesis of 3-thiosubstituted pyrroles from homopropargylic amines and thiosulfonates via a tandem sulfenylation/cyclization has been developed. The thiosulfonates are used both as substrates and oxidants in this transformation. This procedure exhibits good functional group tolerance and a series of 3-thiosubstituted pyrrole derivatives was obtained in moderate to good yields. (Figure presented.).
Regioselective Amine–Borane Cyclization: Towards the Synthesis of 1,2-BN-3-Cyclohexene by Copper-Assisted Triazole/Gold Catalysis
Motika, Stephen E.,Wang, Qiaoyi,Akhmedov, Novruz G.,Wojtas, Lukasz,Shi, Xiaodong
supporting information, p. 11582 - 11586 (2016/10/24)
The combination of triazole/gold (TA-Au) and Cu(OTf)2is identified as the optimal catalytic system for promoting intramolecular hydroboration for the synthesis of a six-membered cyclic amine–borane. Excellent yields (up to 95 %) and regioselectivities (5-exo vs. 6-endo) were achieved through catalyst control and sequential dilution. Good functional-group tolerance was attained, thus allowing the preparation of highly functionalized cyclic amine–borane substrates, which could not be achieved using other methods. Deuterium-labeling studies support the involvement of a hydride addition to a gold-activated alkyne with subsequent C?B bond formation.
Vinyl Cations. 41. Influence of 4-Aryl and 4-Alkyl Substituents on the ?-Route Solvolyses of Homopropargyl Esters
Collins, Clair J.,Hanack, Michael,Stutz, Herbert,Auchter, Gerhard,Schoberth, Winfried
, p. 5260 - 5268 (2007/10/02)
The four 4-substituted-homopropargyl tosylates and triflates 6b-e (R=phenyl, p-tolyl, anisyl, and cyclopropyl) have been synthesized and solvolyzed under various conditions, as have 2-cyclopropyl-1-cyclobutenyl triflate (11-OTf) and nonaflate (11-ONf).In addition, the solvolyses of pent-3-yn-1-yl tosylate (6a-OTs, R=methyl) and triflate (prepared previously) are reported.The ratios of C-3 ring to C-4 ring 3 ring/C4ring)> products are recorded for the reactions in various solvents.As expected, ring closure (kΔ) increases and solvent displacement (kS, SN2) decreases with decreasing nucleophilicity of solvent.Temperature effects are noted for the sovolyses of tosylates 6a-e in 100percent TFE buffered with Na2CO3 in which kΔ increases with increasing temperature.The result is explained by decomposition of the intimate ion pair with temperature, whereupon elimination to the enyne becomes smaller and ring closure (kΔ) increases at the expense of elimination.The possibility of intervention of nonclassical vinyl cations is discussed, as are other mechanistic implications.