- Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis
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Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal-catalyzed cross-coupling of alkyl electrophiles with nitrogen nucleophiles. Described here is an approach to employ tandem photoredox and copper catalysis to enable the cross-coupling of alkyl N-hydroxyphthalimide esters, readily derived from alkyl carboxylic acids, with benzophenone-derived imines. Hydrolysis of the coupling products furnish alkylated primary amines. Primary, secondary, and tertiary alkyl groups can be transferred, and the coupling tolerates a diverse set of functional groups. The method allows rapid functionalization of natural products and drugs, and can be used to expedite syntheses of pharmaceuticals from readily available chemical feedstocks.
- Mao, Runze,Balon, Jonathan,Hu, Xile
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- Direct transformation of secondary amides into secondary amines: Triflic anhydride activated reductive alkylation
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Versatile and mild: The first general method for the title transformation has been developed (see scheme; 2-F-Py=2-fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the r
- Xiao, Kai-Jiong,Wang, Ai-E,Huang, Pei-Qiang
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supporting information; experimental part
p. 8314 - 8317
(2012/09/08)
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