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I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C[double bond, length as m-dash]C bond

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Abstract

A metal-free oxyamination reaction of alkenes with ambient CO2 is reported. In the presence of I2 and DBU, CO2 is applied in situ as a protecting group to regulate the nucleophilicity of the amino group and facilitate the bicyclization of 4-pentenamines with high chemoselectivity. Moreover, this reaction provided a feasible approach to prepare prolinol carbamates with good tolerance of functional groups and high efficiency under mild conditions.

Graphical abstract: I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C [[double bond, length as m-dash]] C bond

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Publication details

The article was received on 03 Jul 2017, accepted on 24 Aug 2017 and first published on 24 Aug 2017


Article type: Communication
DOI: 10.1039/C7GC01992K
Citation: Green Chem., 2017, Advance Article
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    I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C[double bond, length as m-dash]C bond

    S. Wang, X. Zhang, C. Cao, C. Chen and C. Xi, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC01992K

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