- Iron-catalyzed stereoselective haloamidation of amide-tethered alkynes
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In this work, by usingN-methoxybenzamides as efficient acyl nitrene precursors, an iron-catalyzed formalcis-haloamidation of alkyne is reported. Without assistance of additives, the reaction worked well in the presence of 50 mol% FeCl3or FeBr3, leading to a series of chloro/bromo-containing isoindolin-5-ones with high efficiency and wide reaction scope. In the reaction, the iron-facilitated haloamidation proceeds through a halo anion-participating concerted [3+2] cyclization to release the final products. The key intermediate ferric acyl nitreneAis generatedin situfrom a formal removal of MeOH.
- Liu, Jin-Biao,Ren, Miaofeng,Lai, Xiaojing,Qiu, Guanyinsheng
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supporting information
p. 4259 - 4262
(2021/05/05)
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- NBS-mediated aziridination between styrenes and amides under transition metal-free conditions
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An efficient and simple protocol for N-bromosuccinimide (NBS)-mediated styrenes aziridination using amides as the nitrenoid source has been developed. This aziridination affords desired products in moderate to good yields without using transition metal catalyst under very mild reaction condition.
- Meng, Xu,Chen, Wenlin,Zhang, Yuanqing,Chen, Yongxin,Chen, Baohua
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p. 937 - 942
(2014/08/05)
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- Stereoselective Lewis acid mediated (3+2) cycloadditions of N-H- and N-sulfonylaziridines with heterocumulenes
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Alkyl and aryl isothiocyanates and carbodiimides are effective substrates in (3+2) cycloadditions with N-sulfonyl-2-substituted aziridines and 2-phenylaziridine for the synthesis of iminothiazolidines and iminoimidazolidines. Additionally, the stereoselec
- Craig, Robert A.,O'Connor, Nicholas R.,Goldberg, Alexander F. G.,Stoltz, Brian M.
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p. 4806 - 4813
(2014/05/06)
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- Copper-nitrenoid formation and transfer in catalytic olefin aziridination utilizing chelating 2-pyridylsulfonyl moieties
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(Chemical Equation Presented) We have developed an efficient protocol for copper-catalyzed olefin aziridination using 5-methyl-2-pyridinesulfonamide or 2-pyridinesulfonyl azide as the nitrenoid source. The presence of a 2-pyridyl group significantly facil
- Han, Hoon,Seong, Byeong Park,Sang, Kyu Kim,Chang, Sukbok
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p. 2862 - 2870
(2008/09/20)
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- C--H BOND AMINATION AND OLEFIN AZIRIDINATION WITH BETA-DIKETIMINATO COPPER CATALYSTS
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One aspect of the present invention relates to a method for the transition metal (e.g., Cu(I)) mediated amidation of C-H bonds using electron-rich aliphatic azides. In certain embodiments, the methods are useful for the C-H insertion of nitrenes generated and stabilized by a β-diketiminato metal catalyst. In certain embodiments, said nitrenes are generated from organoazides, or by oxidation of the corresponding amine. Another aspect of the present invention relates to olefin aziridination using said β-diketiminato metal catalysts. In addition, the methods of the present invention include stereoselective C-H bond aminations and olefin aziridinatons. In certain embodiments, the methods are conducted in an aerobic environment. In certain embodiments, the present invention relates to the use of O2 as an oxidant, wherein water is the byproduct of oxidation; this fact avoids the generation of toxic byproducts and renders the methods atom economical.
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Page/Page column 52
(2008/12/06)
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