Adamantane-1-Carbonyl-Directed C–H Borylation and Hydroxylation of Benzenethiols

A novel route has been described for C–H borylation and hydroxylation of benzenethiols directed by adamantane-1-carbonyl using BBr3. The protocol generates corresponding arylboronic esters and phenols in moderate to excellent yields under metal-free conditions. In addition, the borylated product can...

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Published inOrganic letters Vol. 24; no. 39; pp. 7163 - 7167
Main Authors Xu, Xiaobo, Wu, Gaorong, Yang, Zhaoziyuan, Liu, Xian, Hao, Liqiang, Wang, Yangyang, Ma, Zhihong, Ji, Yafei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.10.2022
Amer Chemical Soc
Subjects
Adamantane
Chemistry
Chemistry, Organic
Hydroxylation
Phenols
Physical Sciences
Science & Technology
Sulfhydryl Compounds
CHEMISTRY
THIOLS
COMPLEXES
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Summary:A novel route has been described for C–H borylation and hydroxylation of benzenethiols directed by adamantane-1-carbonyl using BBr3. The protocol generates corresponding arylboronic esters and phenols in moderate to excellent yields under metal-free conditions. In addition, the borylated product can be transformed and the directing group can be removed in good yields, which will facilitate the synthesis of structurally diverse benzenethiols.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02858