- Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction
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A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.
- Zhang, Xiao,Lu, Guo-Ping,Cai, Chun
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p. 5580 - 5585
(2016/10/21)
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- An odorless, one-pot synthesis of nitroaryl thioethers via SNAr reactions through the in situ generation of S-alkylisothiouronium salts
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A newly developed C-S bond formation nucleophilic aromatic substitution (SNAr) reaction in aqueous Triton X-100 (TX100) micelles has been disclosed. This chemistry, in which odorless, cheap and stable thiourea in place of thiols is used as the sulfur reagent, provides an efficient approach for the generation of nitroaryl thioethers, which are useful structural units of many bioactive molecules, rendering this methodology attractive to both synthetic and medicinal chemistry.
- Lu, Guo-Ping,Cai, Chun
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p. 59990 - 59996
(2015/02/19)
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- Dynamic kinetic resolution of allylic sulfoxides by Rh-catalyzed hydrogenation: A combined theoretical and experimental mechanistic study
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A dynamic kinetic resolution (DKR) of allylic sulfoxides has been demonstrated by combining the Mislow [2,3]-sigmatropic rearrangement with catalytic asymmetric hydrogenation. The efficiency of our DKR was optimized by using low pressures of hydrogen gas to decrease the rate of hydrogenation relative to the rate of sigmatropic rearrangement. Kinetic studies reveal that the rhodium complex acts as a dual-role catalyst and accelerates the substrate racemization while catalyzing olefin hydrogenation. Scrambling experiments and theoretical modeling support a novel mode of sulfoxide racemization which occurs via a rhodium π-allyl intermediate in polar solvents. In nonpolar solvents, however, the substrate racemization is primarily uncatalyzed. Computational studies suggest that the sulfoxide binds to rhodium via O-coordination throughout the catalytic cycle for hydrogenation.
- Dornan, Peter K.,Kou, Kevin G. M.,Houk,Dong, Vy M.
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supporting information
p. 291 - 298
(2014/01/23)
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- MoO2Cl2(dmf)2-catalyzed domino reactions of ω-nitro alkenes to 3,4-Dihydro-2 H -1,4-benzothiazines and Other Heterocycles
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Using the transformation of allyl 2-nitrophenyl thioethers to 3,4-dihydro-2H-1,4-benzothiazines as an example the reductive cyclization of -nitroalkenes to saturated N-heterocycles can be performed highly selective and with high yields if a combination of
- Malakar, Chandi C.,Merisor, Elena,Conrad, Jürgen,Beifuss, Uwe
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experimental part
p. 1766 - 1770
(2010/10/20)
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