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Metal-Free Aziridination of Styrene Derivatives with Iminoiodinane Catalyzed by a Combination of Iodine and Ammonium Iodide

Kensuke Kiyokawa, Tomoki Kosaka and Satoshi Minakata*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Email: minakatachem.eng.osaka-u.ac.jp

K. Kiyokawa, T. Kosaka, S. Minataka, Org. Lett., 2013, 15, 4858-4861.

DOI: 10.1021/ol402276f



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Abstract

A metal-free catalytic aziridination of styrene derivatives with N-tosyliminophenyliodinane (PhI=NTs) is promoted by a combination of I2 and tetrabutylammonium iodide (TBAI). TBAI3 as highly efficient catalyst as well as N,N-diiodotosylamide as actual aziridination reagent are generated in situ.

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Key Words

aziridination


ID: J54-Y2013