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Issue 8, 2019
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Efficient metal-free aminoiodination of alkenes with N-fluorobenzenesulfonimide under mild conditions

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Abstract

A novel efficient metal-free aminoiodination of alkenes with N-fluorobenzenesulfonimide (NFSI) through an iodonium intermediate under mild conditions with good regioselectivity and stereoselectivity is reported. Unlike transition-metal catalysed aminative bisfunctionalization with NFSI in which the oxidative addition of NFSI to transition-metals affords an electrophilic amino radical, the oxidation of anionic iodide by NFSI in situ generates an electrophilic iodine cation and an amino nucleophile to fulfil this efficient reaction. 2,2,6,6-Tetramethyl-piperidine-1-oxyl (TEMPO) could considerably promote this iodoamination at room temperature. A preliminary trial suggests that bromoamination could also be achieved under similar conditions.

Graphical abstract: Efficient metal-free aminoiodination of alkenes with N-fluorobenzenesulfonimide under mild conditions

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Supplementary files

Article information


Submitted
04 Dec 2018
Accepted
23 Jan 2019
First published
23 Jan 2019

Org. Biomol. Chem., 2019,17, 2126-2133
Article type
Paper

Efficient metal-free aminoiodination of alkenes with N-fluorobenzenesulfonimide under mild conditions

B. Lei, Q. Miao, L. Ma, R. Fu, F. Hu, N. Ni and Z. Li, Org. Biomol. Chem., 2019, 17, 2126
DOI: 10.1039/C8OB03019G

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