Lewis Acid-Conjugated Pyrene Photoredox Catalyst Promoting the Addition Reaction of α-Silyl Amines with Benzalmalononitriles

We developed the addition reaction of α-silyl amines with benzalmalononitriles catalyzed by a Mg2+-conjugated pyrene catalyst under visible light irradiation. The catalytic activity of this complex was higher than pyrene alone, a Mg2+ Lewis acid alone, and the sum of these two independent catalytic...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 70; no. 11; pp. 765 - 768
Main Authors Katayama, Yuri, Mitsunuma, Harunobu, Kanai, Motomu
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 01.11.2022
Japan Science and Technology Agency
Subjects
Amines
Catalysts
Catalytic activity
Electron transfer
Electrostatic properties
Lewis acid
Light irradiation
Magnesium
Photoredox catalysis
photoredox catalyst
Pyrene
single electron transfer
Single electrons
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Summary:We developed the addition reaction of α-silyl amines with benzalmalononitriles catalyzed by a Mg2+-conjugated pyrene catalyst under visible light irradiation. The catalytic activity of this complex was higher than pyrene alone, a Mg2+ Lewis acid alone, and the sum of these two independent catalytic elements. The observed enhancement in catalytic activity was likely due to electrostatic interactions of the Mg2+ Lewis acid with the pyrene radical anion, which was generated through photoinduced single electron transfer from α-silyl amines to the catalyst’s pyrene moiety.
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c22-00526