Tetrahedron letters2022,Vol.1016.DOI:10.1016/j.tetlet.2022.153921

"Stacked-arene"-type organocatalysts: Utilization of p-p interaction as an electron tuning tool

Yamamoto, Yuki Inoue, Aiko Sakai, Dan Otawa, Yuna Mori, Keiji
Tetrahedron letters2022,Vol.1016.DOI:10.1016/j.tetlet.2022.153921

"Stacked-arene"-type organocatalysts: Utilization of p-p interaction as an electron tuning tool

Yamamoto, Yuki 1Inoue, Aiko 1Sakai, Dan 1Otawa, Yuna 1Mori, Keiji1
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作者信息

  • 1. Tokyo Univ Agr & Technol
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Abstract

We have developed a novel type of organocatalyst having a 1,8 diarylnaphthalene core, namely, a "Stacked-arene "-type organocatalyst. The key point of the catalyst design is the pi-pi interaction based electron tuning. This through space electron tuning effect is effective enough for the improvement of the catalytic activity (reducing the catalyst loading), and this tendency was evaluated by the Michael addition reaction between nitrostyrene and dimethyl malonate. Additional experiments suggest that the expected improvement of the hydrogen bonding ability plays a critical role in the high performance of the designed catalyst. (C) 2022 Elsevier Ltd. All rights reserved.

Key words

pi-pi interaction/Stacked arene/Organocatalyst/Thiourea/ANION-PI/ASYMMETRIC CATALYSIS/STEREOGENIC CENTERS/DIELS-ALDER/CATION/DESIGN/PROPIOLOYLPYRAZOLES/CYCLOADDITION/ACTIVATION

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN:0040-4039
参考文献量43
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