A Copper‐Catalyzed Tandem C–H ortho ‐Hydroxylation and N–N Bond‐Formation Transformation: Expedited Synthesis of 1‐( ortho ‐Hydroxyaryl)‐1 H ‐indazoles

A facile, one‐pot synthesis of 1 H ‐indazoles featuring a Cu‐catalyzed C–H ortho ‐hydroxylation and N–N bond‐formation sequence with the use of pure oxygen as the terminal oxidant was developed. The reaction of readily available 2‐arylaminobenzonitriles with various organometallic reagents led to or...

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Published inEuropean journal of organic chemistry Vol. 2017; no. 45; pp. 6604 - 6608
Main Authors Chen, Cheng‐yi, He, Fengxian, Tang, Guangrong, Ding, Han, Wang, Zhaobin, Li, Dawei, Deng, Lujiang, Faessler, Roger
Format Journal Article
LanguageEnglish
Published 08.12.2017
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Summary:A facile, one‐pot synthesis of 1 H ‐indazoles featuring a Cu‐catalyzed C–H ortho ‐hydroxylation and N–N bond‐formation sequence with the use of pure oxygen as the terminal oxidant was developed. The reaction of readily available 2‐arylaminobenzonitriles with various organometallic reagents led to ortho ‐arylamino N–H ketimine species. Subsequent Cu‐catalyzed hydroxylation at the ortho position of the aromatic ring followed by N–N bond formation in DMSO under a pure‐oxygen atmosphere afforded a wide variety of 1‐( ortho ‐hydroxyaryl)‐1 H ‐indazoles in good to excellent yields. This efficient method does not require the utilization of noble‐metal catalysts, elaborate directing groups, or privileged ligands.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701149