4.7 Article

Substituent-Directed Regioselective Azidation: Copper-Catalyzed C-H Azidation and Iodine-Catalyzed Dearomatizative Azidation of Indole

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JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 1, 页码 228-235

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02591

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  1. SERB, New Delhi [SB/S1/OC-56/2013]
  2. CSIR, New Delhi [02(0226)15/EMR-II]
  3. Indian Institute of Science
  4. RL Fine Chem, Bangalore
  5. Synovation Chemicals, and Sourcing Pvt Ltd., Bangalore
  6. CSIR, New Delhi

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Azidation of indoles using iodine and copper bromide as catalysts under ambient reaction conditions is presented. The regioselectivity is directed by the substituent at the C3-position of indole. A radical stabilizing group such as an ester or ketone moiety at the C3-position of indole leads to azidation at the C2-position, whereas a less radical stabilizing group such as an alkyl or amide group at the C3-position of indole furnishes the 3-azidooxindole product. This protocol is mild and efficient to obtain several 2-azidoindole derivatives and 3-azidooxindole derivatives in moderate to good yields. The reaction conditions hold well for gram-scale synthesis.

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