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Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.

Publication ,  Journal Article
Ortiz, GX; Hemric, BN; Wang, Q
Published in: Organic letters
March 2017

Selective C-H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl2. Interestingly, analogous reactions in the absence of ZnCl2 resulted in the formation of indole aminal products.

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Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

March 2017

Volume

19

Issue

6

Start / End Page

1314 / 1317

Related Subject Headings

  • Zinc Compounds
  • Stereoisomerism
  • Organic Chemistry
  • Indoles
  • Chlorides
  • Catalysis
  • Benzenesulfonates
  • Amines
  • Amides
  • 34 Chemical sciences
 

Citation

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Ortiz, G. X., Hemric, B. N., & Wang, Q. (2017). Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides. Organic Letters, 19(6), 1314–1317. https://doi.org/10.1021/acs.orglett.7b00358
Ortiz, Gerardo X., Brett N. Hemric, and Qiu Wang. “Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.Organic Letters 19, no. 6 (March 2017): 1314–17. https://doi.org/10.1021/acs.orglett.7b00358.
Ortiz GX, Hemric BN, Wang Q. Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides. Organic letters. 2017 Mar;19(6):1314–7.
Ortiz, Gerardo X., et al. “Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.Organic Letters, vol. 19, no. 6, Mar. 2017, pp. 1314–17. Epmc, doi:10.1021/acs.orglett.7b00358.
Ortiz GX, Hemric BN, Wang Q. Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides. Organic letters. 2017 Mar;19(6):1314–1317.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

March 2017

Volume

19

Issue

6

Start / End Page

1314 / 1317

Related Subject Headings

  • Zinc Compounds
  • Stereoisomerism
  • Organic Chemistry
  • Indoles
  • Chlorides
  • Catalysis
  • Benzenesulfonates
  • Amines
  • Amides
  • 34 Chemical sciences