Journal
ORGANIC LETTERS
Volume 17, Issue 24, Pages 6130-6133Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03147
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Funding
- American Chemical Society [53951-DNI1]
- National Science Foundation [CHE-1455220]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1455220] Funding Source: National Science Foundation
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A novel approach toward the synthesis of sterically hindered o-aminophenols has been achieved by a formal aryne insertion into hydroxyindolinones. This transformation offers a rapid and efficient entry to diverse o-aminophenol scaffolds under mild transition-metal-free conditions. The reaction involves the addition of hydroxyindolinones to arynes followed by a chemo- and regioselective [1,3]-rearrangement. Furthermore, the reactions of N-hydroxyindoles and arynes were found to provide the C3-aryl indole products via an alternative [3,3]-rearrangement pathway.
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