4.8 Article

Conversion of Cyclic Ketones to 2,3-Fused Pyrroles and Substituted Indoles

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 32, Pages 11712-11715

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja405043g

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Funding

  1. National Science Foundation [CHE 1213246]
  2. Division Of Chemistry
  3. Direct For Mathematical & Physical Scien [1213246] Funding Source: National Science Foundation

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A highly effective synthesis of 2,3-fused pyrroles from cyclic ketones has been achieved. The transformation includes a rhodium-catalyzed reaction of 4-alkenyl-1-sulfonyl-1,2,3-triazoles featuring an unusual 4 pi electrocyclization. The methodology was further extended to the synthesis of indoles using a one-pot reaction starting from 1-ethynylcyclohexenes.

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