Issue 19, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
03 Jul 2017
Accepted
24 Aug 2017
First published
24 Aug 2017

Green Chem., 2017,19, 4515-4519

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, 19, 4515 DOI: 10.1039/C7GC01992K

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