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

Xiaobo Xu, Gaorong Wu, Zhaoziyuan Yang, Xian Liu, Liqiang Hao, Yangyang Wang, Zhihong Ma, Yafei Ji

Organic letters 2022 Oct 07

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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.

Citation

Xiaobo Xu, Gaorong Wu, Zhaoziyuan Yang, Xian Liu, Liqiang Hao, Yangyang Wang, Zhihong Ma, Yafei Ji. Adamantane-1-Carbonyl-Directed C-H Borylation and Hydroxylation of Benzenethiols. Organic letters. 2022 Oct 07;24(39):7163-7167