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Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones.

Publication ,  Journal Article
Chen, Z; Wang, Q
Published in: Organic letters
December 2015

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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Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

December 2015

Volume

17

Issue

24

Start / End Page

6130 / 6133

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Chen, Z., & Wang, Q. (2015). Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones. Organic Letters, 17(24), 6130–6133. https://doi.org/10.1021/acs.orglett.5b03147
Chen, Zhilong, and Qiu Wang. “Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones.Organic Letters 17, no. 24 (December 2015): 6130–33. https://doi.org/10.1021/acs.orglett.5b03147.
Chen, Zhilong, and Qiu Wang. “Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones.Organic Letters, vol. 17, no. 24, Dec. 2015, pp. 6130–33. Epmc, doi:10.1021/acs.orglett.5b03147.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

December 2015

Volume

17

Issue

24

Start / End Page

6130 / 6133

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences