Controlled Regioselective Amination of Peryleneimides

Lijo George; Zafar Ahmed; Helge Lemmetyinen; Alexander Efimov

doi:10.1002/ejoc.201403299

Controlled Regioselective Amination of Peryleneimides

Lijo George, Zafar Ahmed, Helge Lemmetyinen, Alexander Efimov

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Abstract

Perylenediimides (PDIs) and perylenemonoimide diesters (PMIs) can be selectively substituted at the 1,6- or 7,12-positions of the bay region, respectively, by direct amination reactions. The reactions proceed by the formation of a perylene radical anion and its subsequent oxidation, and the yields range from 20-97%. The amination can be tuned to obtain either mono- or disubstituted perylenes by varying the oxidants involved. The presence of the imide cycle is crucial for the transformation, although the amination occurs regioselectively at the bay-region positions distant from the imide cycle.

Translated title of the contribution	Controlled Regioselective Amination of Peryleneimides
Original language	English
Pages (from-to)	584-590
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	3
Early online date	12 Dec 2014
DOIs	https://doi.org/10.1002/ejoc.201403299
Publication status	Published - 14 Jan 2015
Publication type	A1 Journal article-refereed

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title = "Controlled Regioselective Amination of Peryleneimides",

abstract = "Perylenediimides (PDIs) and perylenemonoimide diesters (PMIs) can be selectively substituted at the 1,6- or 7,12-positions of the bay region, respectively, by direct amination reactions. The reactions proceed by the formation of a perylene radical anion and its subsequent oxidation, and the yields range from 20-97%. The amination can be tuned to obtain either mono- or disubstituted perylenes by varying the oxidants involved. The presence of the imide cycle is crucial for the transformation, although the amination occurs regioselectively at the bay-region positions distant from the imide cycle.",

author = "Lijo George and Zafar Ahmed and Helge Lemmetyinen and Alexander Efimov",

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T1 - Controlled Regioselective Amination of Peryleneimides

AU - George, Lijo

AU - Ahmed, Zafar

AU - Lemmetyinen, Helge

AU - Efimov, Alexander

N1 - Article first published online: 12 DEC 2014 Contribution: organisation=keb,FACT1=1 Portfolio EDEND: 2014-12-30 Publisher name: Wiley - V C H Verlag GmbH & Co. KGaA

PY - 2015/1/14

Y1 - 2015/1/14

N2 - Perylenediimides (PDIs) and perylenemonoimide diesters (PMIs) can be selectively substituted at the 1,6- or 7,12-positions of the bay region, respectively, by direct amination reactions. The reactions proceed by the formation of a perylene radical anion and its subsequent oxidation, and the yields range from 20-97%. The amination can be tuned to obtain either mono- or disubstituted perylenes by varying the oxidants involved. The presence of the imide cycle is crucial for the transformation, although the amination occurs regioselectively at the bay-region positions distant from the imide cycle.

AB - Perylenediimides (PDIs) and perylenemonoimide diesters (PMIs) can be selectively substituted at the 1,6- or 7,12-positions of the bay region, respectively, by direct amination reactions. The reactions proceed by the formation of a perylene radical anion and its subsequent oxidation, and the yields range from 20-97%. The amination can be tuned to obtain either mono- or disubstituted perylenes by varying the oxidants involved. The presence of the imide cycle is crucial for the transformation, although the amination occurs regioselectively at the bay-region positions distant from the imide cycle.

U2 - 10.1002/ejoc.201403299

DO - 10.1002/ejoc.201403299

M3 - Article

SN - 1434-193X

VL - 2015

SP - 584

EP - 590

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 3

ER -

Controlled Regioselective Amination of Peryleneimides

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