4.8 Article

I2/FeCl3-Catalyzed Domino Reaction of Aurones with Enamino Esters for the Synthesis of Highly Functionalized Pyrroles

Journal

ORGANIC LETTERS
Volume 24, Issue 25, Pages 8406-8411

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03537

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Funding

  1. Natural Science Foundation of Anhui Province [2008085QB64]
  2. Foundation of Anhui Province Key Laboratory of Clean Energy Materials and Chemistry for Sustainable Conversion of Natural Resources [LCECSC-15]
  3. Foundation of Anhui Polytechnic University [Xjky2020079]

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A novel and efficient multi-component reaction has been developed for the synthesis of polysubstituted pyrroles. This protocol offers several advantages including mild reaction conditions, broad substrate scope, and high efficiency.
A novel and efficient I2/FeCl3-catalyzed domino reaction of aurones with enamino esters via Michael addition, iodination, intramolecular nucleophilic substitution, and spiro ring opening processes has been developed, affording a vast variety of polysubstituted pyrroles in moderate to excellent yields. This protocol features mild reaction conditions, broad substrate scope, high atom economy and efficiency, and feasibility for large-scale synthesis. A plausible mechanism for the pyrrole synthesis is proposed.

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