- Heterogeneously catalyzed oxidative cyanation of tertiary amines with sodium cyanide/hydrogen peroxide using polymer-supported iron(II) phthalocyanines as catalyst
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The first report on heterogeneously catalyzed oxidative cyanation of various tertiary amines to the corresponding a-amino nitriles with high yields and selectivity by using hydrogen peroxide oxidant in presence of sodium cyanide and Fe(II) phthalocyanine supported on a polymer as catalyst is described. The present method has the added benefits of facile recovery of the catalyst from the reaction mixture and its subsequent use without further activation. Consistent catalytic activity with no metal leaching was observed during this course.
- Singhal, Sweety,Jain, Suman L.,Sain, Bir
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- Iron-Catalyzed α-C-H Cyanation of Simple and Complex Tertiary Amines
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This manuscript details the development of a general and mild protocol for the α-C-H cyanation of tertiary amines and its application in late-stage functionalization. Suitable substrates include tertiary aliphatic, benzylic, and aniline-type substrates and complex substrates. Functional groups tolerated under the reaction conditions include various heterocycles and ketones, amides, olefins, and alkynes. This broad substrate scope is remarkable, as comparable reaction protocols for α-C-H cyanation frequently occur via free radical mechanisms and are thus fundamentally limited in their functional group tolerance. In contrast, the presented catalyst system tolerates functional groups that typically react with free radicals, suggesting an alternative reaction pathway. All components of the described catalyst system are readily available, allowing implementation of the presented methodology without the need for lengthy catalyst synthesis.
- Yilmaz, Ozgur,Dengiz, Cagatay,Emmert, Marion H.
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supporting information
p. 2489 - 2498
(2021/02/06)
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- Nano cobalt-copper ferrite catalyzed regioselective α-C(sp3)–H cyanation of amines: Secondary, tertiary, and drug molecules
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Oxidative cyanation of sp3C–H bonds at the α position of amines was achieved using CoCuFe2O4 as a catalyst and NaCN as an inexpensive cyanide source at room temperature. CoCuFe2O4 was found to be an active catalyst for Csp [3]-Csp coupling, efficiently delivering valuable α-aminonitriles from tertiary/secondary amines in good yields. The corresponding products were obtained with high selectivity toward α position. In addition, functional group tolerance offered the opportunity for application in late-stage functionalization of biologically active molecules. This transformation proceeds convenient on a gram-scale, and the catalyst can be reused for several runs with consistent catalytic activity.
- Heidarian, Mahdi,Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh
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- Cobalt-Catalyzed oxidative α-cyanation of tertiary aromatic amines with trimethylsilyl cyanide and tert -butyl hydroperoxide
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In this Letter is described that a cobalt(II)-tert-butyl hydroperoxide oxidizing system was used to catalyze the α-cyanation of aromatic tertiary amines in the presence of trimethylsilyl cyanide to produce the corresponding α-aminonitriles in good yields. Georg Thieme Verlag Stuttgart. New York.
- Sakai, Norio,Mutsuro, Akihiro,Ikeda, Reiko,Konakahara, Takeo
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p. 1283 - 1285
(2013/07/19)
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- Iron catalyzed oxidative cyanation of tertiary amines
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Iron(ii) and iron(iii) salts catalyze the oxidative α-cyanation of tertiary amines by trimethylsilyl cyanide in the presence of tert-butylhydroperoxide under acid-free conditions at room temperature.
- Han, Wei,Ofial, Armin R.
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supporting information; experimental part
p. 5024 - 5026
(2010/01/06)
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