4.8 Article

Synthesis of Cyclopentene Derivatives via Electrochemically Induced Intermolecular Selective (3+2) Annulation

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 35, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202207059

Keywords

Alkynes; (3+2) Annulation; Cyclopentenes; Electrochemistry; Mediator

Funding

  1. China Postdoctoral Science Foundation [2021M702516]
  2. National Key R&D Program of China [2021YFA1500104]
  3. National Natural Science Foundation of China [22031008]
  4. Science Foundation of Wuhan [2020010601012192]

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In this study, an electrochemical mediator-induced intermolecular selective (3+2) annulation was developed for the synthesis of a library of decorated cyclopentenes and cyclopentanes. This method offers high efficiency, mild reaction conditions, broad substrate scope, good functional group tolerance, and high regioselectivity.
Cyclopentenes are common cores in many natural products, and in bioactive and functional molecules. However, their synthesis remains challenging in terms of harsh conditions, poor selectivity, prefunctionalization of the substrates, over-reliance on volatile activating reagents and the use of noble metals. Herein, we develop an electrochemical mediator-induced intermolecular selective (3+2) annulation of readily available alkenes and alkynes/alkenes, which provides a simple and efficient method for the synthesis of a library of decorated cyclopentenes and cyclopentanes. This protocol features high efficiency, mild reaction conditions, broad substrate scope, good functional group tolerance, and high regioselectivity. Potential applications are demonstrated by gram-scale synthesis as well as the construction of structural diversity and complexity. A preliminary mechanistic investigation was performed, which indicated that an iodine radical and carbon radicals are involved in this transformation.

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