ortho-Functionalization of Pillar[5]arene: An Approach to Mono-ortho-Alkyl/Aryl-Substituted A1/A2-Dihydroxypillar[5]arene

Despite the fact that the rim and lateral functionalizations of pillar[n]arenes have been well explored, ortho-functionalization has rarely been realized. In this work, we report a facile method of introducing a single functionality ortho to the hydroxyl group in A1/A2-dihydroxypillar[5]arene via a...

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Published inOrganic letters Vol. 24; no. 9; pp. 1822 - 1826
Main Authors Wang, Zhuo, Liu, Yahu A., Yang, Hui, Hu, Wei-Bo, Wen, Ke
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 11.03.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID
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Summary:Despite the fact that the rim and lateral functionalizations of pillar[n]arenes have been well explored, ortho-functionalization has rarely been realized. In this work, we report a facile method of introducing a single functionality ortho to the hydroxyl group in A1/A2-dihydroxypillar[5]arene via a Grignard addition to pillar[4]arene[1]quinone followed by a dienone-phenol rearrangement. The described ortho-alkylation/arylation method allowed formation of various mono ortho-alkyl/aryl-substituted A1/A2-dihydroxypillarNarenes previously difficult to obtain.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00272