4.5 Article

Efficient and Functional-Group-Tolerant Synthesis of Substituted Furans through the Pd-Catalyzed 5-exo-dig Cyclization/Coupling of γ-Acetylenic β-Keto Esters with (Hetero)Aryl Bromides

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 20-21, Pages 2554-2560

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800046

Keywords

Oxygen heterocycles; Palladium; Homogeneous catalysis; Cyclization; Synthetic methods

Funding

  1. Polish National Science Centre [DEC-2016/22/E/ST5/00537]
  2. Polish Ministry of Science and Higher Education

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We report an efficient protocol for the synthesis of 2,3,5-trisubstituted furans through the reaction of readily available -acetylenic -keto esters with aryl and heteroaryl bromides. The reaction, which involves a 5-exo-dig cyclization, coupling, and isomerization of a double bond, proceeds smoothly with very low catalyst loading (0.1 mol-%), and shows excellent functional-group tolerance.

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