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二芳基碘鎓（III）盐与自由基的反应实现了萘酚的一锅法双芳基化反应。

The Diaryliodonium(III) Salts Reaction With Free-Radicals Enables One-Pot Double Arylation of Naphthols.

作者信息

Satkar Yuvraj, Wrobel Kazimierz, Trujillo-González Daniel E, Ortiz-Alvarado Rafael, Jiménez-Halla J Oscar C, Solorio-Alvarado César R

机构信息

División de Ciencias Naturales y Exactas, Departamento de Química, Universidad de Guanajuato, Guanajuato, Mexico.

Facultad de Químico Farmacobiología, Universidad Michoacana de San Nicolás de Hidalgo, Morelia, Mexico.

出版信息

Front Chem. 2020 Oct 15;8:563470. doi: 10.3389/fchem.2020.563470. eCollection 2020.

DOI:10.3389/fchem.2020.563470
PMID:33195052
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7593783/
Abstract

The chemoselective reaction of the - followed by the centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot doubly arylation of naphthols through the sequential - /O- bond formation. The naphthyl radicals were generated in the reaction by the tetramethylpiperidinyl radical (TMP·) which resulted from the homolytic fragmentation of the precursor TMPO. Experimental and DFT calculations provided a complete panorama of the reaction mechanism.

摘要

描述了萘基自由基与二芳基碘鎓（III）盐中电子缺乏程度更高的高价键的化学选择性反应。这种发现的反应性构成了二芳基碘鎓（III）盐的一种新的活化模式，通过依次形成C−C / O−C键实现了萘酚的一锅法双芳基化。反应中，萘基自由基由前体TMPO均裂产生的四甲基哌啶基自由基（TMP·）生成。实验和DFT计算提供了完整的反应机理全景。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/34650874044f/fchem-08-563470-g0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/a4cd66ce6ef0/fchem-08-563470-g0001.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/9f9650f06ee3/fchem-08-563470-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/4ab02923d6cc/fchem-08-563470-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/34650874044f/fchem-08-563470-g0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/a4cd66ce6ef0/fchem-08-563470-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/a5acd25613cd/fchem-08-563470-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/f353439dc3fd/fchem-08-563470-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/f1a1f30eb1f5/fchem-08-563470-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/9f9650f06ee3/fchem-08-563470-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/4ab02923d6cc/fchem-08-563470-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9e8/7593783/34650874044f/fchem-08-563470-g0007.jpg

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