- External Oxidant-Free Oxidative Tandem Cyclization: NaI-Catalyzed Thiolation for the Synthesis of 3-Thiosubstituted Pyrroles
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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.).
- Yuan, Bingxiang,Jiang, Yong,Qi, Zhenjie,Guan, Xin,Wang, Ting,Yan, Rulong
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supporting information
p. 5112 - 5117
(2019/11/11)
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- Tert-Butyl Nitrite Promoted Oxidative Intermolecular Sulfonamination of Alkynes to Synthesize Substituted Sulfonyl Pyrroles from the Alkynylamines and Sulfinic Acids
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tert-Butyl nitrite promoted oxidative intermolecular sulfonamination of alkynes to synthesize substituted sulfonyl pyrroles from the alkynylamines and sulfinic acids via tandem addition/cyclization was developed. This reaction is performed well by employing tert-butyl nitrite as the oxidant, and various substituted sulfonyl pyrroles are formed in moderate to good yields with no requirement of metal catalysis.
- Qi, Zhenjie,Jiang, Yong,Wang, Yanyan,Yan, Rulong
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supporting information
p. 8636 - 8644
(2018/06/18)
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- Cu-Catalyzed Tandem Aerobic Oxidative Cyclization for the Synthesis of 3,3′-Bipyrroles from the Homopropargylic Amines
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A Cu-catalyzed method for the synthesis of 3,3′-bipyrroles from homopropargylic amines through tandem aerobic oxidative cyclization involving the formation of C-C bond has been developed. The features of this reaction are a small number of Cu catalysis and simple starting substrates. Moreover, this procedure exhibits good functional group tolerance and a series of 3,3′-bipyrroles derivatives are obtained in moderate to good yields.
- Qi, Zhenjie,Jiang, Yong,Yuan, Bingxiang,Niu, Yanning,Yan, Rulong
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supporting information
p. 5048 - 5052
(2018/08/24)
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- Vinyl Cations. 41. Influence of 4-Aryl and 4-Alkyl Substituents on the ?-Route Solvolyses of Homopropargyl Esters
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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.
- Collins, Clair J.,Hanack, Michael,Stutz, Herbert,Auchter, Gerhard,Schoberth, Winfried
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p. 5260 - 5268
(2007/10/02)
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