Boron-mediated directed aromatic C–H hydroxylation View Full Text


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Article Info

DATE

2020-03-12

AUTHORS

Jiahang Lv, Binlin Zhao, Yu Yuan, Ying Han, Zhuangzhi Shi

ABSTRACT

Transition metal-catalysed C–H hydroxylation is one of the most notable advances in synthetic chemistry during the past few decades and it has been widely employed in the preparation of alcohols and phenols. The site-selective hydroxylation of aromatic C–H bonds under mild conditions, especially in the context of substituted (hetero)arenes with diverse functional groups, remains a challenge. Here, we report a general and mild chelation-assisted C–H hydroxylation of (hetero)arenes mediated by boron species without the use of any transition metals. Diverse (hetero)arenes bearing amide directing groups can be utilized for ortho C–H hydroxylation under mild reaction conditions and with broad functional group compatibility. Additionally, this transition metal-free strategy can be extended to synthesize C7 and C4-hydroxylated indoles. By utilizing the present method, the formal synthesis of several phenol intermediates to bioactive molecules is demonstrated. More... »

PAGES

1316

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/s41467-020-15207-x

DOI

http://dx.doi.org/10.1038/s41467-020-15207-x

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1125562661

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/32165636


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