Issue 20, 2016

PIDA–I2 mediated direct vicinal difunctionalization of olefins: iodoazidation, iodoetherification and iodoacyloxylation

Abstract

Iodinium cation (I+ or IOAc) was produced from the combination of phenyliodine diacetate (PIDA) and iodine. I+ facilitated the direct vicinal difunctionalization of olefins to α-azido, α-trideuteriomethoxy, α-2,2,2-trifluoroethoxy and α-acyloxy alkyl iodides via cation–π interaction at room temperature and under transition-metal free conditions.

Graphical abstract: PIDA–I2 mediated direct vicinal difunctionalization of olefins: iodoazidation, iodoetherification and iodoacyloxylation

Supplementary files

Article information

Article type
Paper
Submitted
10 Mac 2016
Accepted
15 Apr 2016
First published
15 Apr 2016

Org. Biomol. Chem., 2016,14, 4654-4663

PIDA–I2 mediated direct vicinal difunctionalization of olefins: iodoazidation, iodoetherification and iodoacyloxylation

T. K. Achar, S. Maiti and P. Mal, Org. Biomol. Chem., 2016, 14, 4654 DOI: 10.1039/C6OB00532B

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