- SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution
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A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.
- Liao, Xudong,Zhou, Yi,Ai, Chengmei,Ye, Cuijiao,Chen, Guanghui,Yan, Zhaohua,Lin, Sen
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supporting information
(2021/11/01)
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- A Green Chemoenzymatic Process for the Synthesis of Azoxybenzenes
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An efficient chemoenzymatic process for the synthesis of azoxybenzenes was developed. A peracid was generated in situ by Novozym 435, and then a range of anilines were oxidized by the produced peracid to afford azoxybenzenes in yields ranging from 63.1 to 94.1 %. This method expands the application of lipase in organic synthesis and provides an alternative method for the synthesis of azoxybenzenes.
- Yang, Fengjuan,Wang, Zhi,Zhang, Xiaowen,Jiang, Liyan,Li, Yazhuo,Wang, Lei
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p. 3450 - 3453
(2015/11/10)
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- Gold-catalyzed cyclization/oxidative [3+2] cycloadditions of 1,5-enynes with nitrosobenzenes without additional oxidants
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Golden control: The title reaction (see scheme) proceeds with high stereocontrol to generate the heterocyclic products in good yield. Experiments to probe the mechanism were performed. Copyright
- Chen, Chun-Hao,Tsai, Yen-Ching,Liu, Rai-Shung
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supporting information
p. 4599 - 4603
(2013/05/21)
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- Synthesis of o-(diphenylphosphinoyloxy)anilines by the rhodium-catalyzed reaction of nitroarenes and diphenylphosphine oxide
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A rhodium complex Rh2(OAc)4 catalyzed the reaction of nitrobenzenes and diphenylphosphine oxide HP({double bond, long}O)Ph2 giving o-(diphenylphosphinoyloxy)anilines predominantly, which were accompanied by small amounts of the p-isomers. Nitorobenzenes possessing a bulky o-substituent, particularly o-(t-butyl)nitrobenzenes, underwent the reaction in high yields. The reaction is considered to involve the reductive formation of O-phosphinoyl-N-arylhydroxyamines from nitrobenzenes, and o-phosphinoyloxylation by the rearrangement.
- Arisawa, Mieko,Kuwajima, Manabu,Yamaguchi, Masahiko
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supporting information; experimental part
p. 3116 - 3118
(2010/08/07)
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