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Synthesis 2016; 48(12): 1865-1871
DOI: 10.1055/s-0035-1560432
DOI: 10.1055/s-0035-1560432
special topic
Furans to Benzofurans: Intramolecular Cross-Benzoin Reactions Catalysed by N-Heterocyclic Carbenes
Autoren
Weitere Informationen
Publikationsverlauf
Received: 24. Februar 2016
Accepted after revision: 08. März 2016
Publikationsdatum:
15. April 2016 (online)
Abstract
The first synthesis of dihydrobenzofuranones and benzofurans based on an intramolecular cross-benzoin reaction has been reported. Commercially available 3-furan carboxaldehydes are readily α-alkylated to furnish 3-formyl-2-furylcarbinols, which are further elaborated to the synthesis of benzofurans in good yields through sequential bismuth(III) chloride catalysed furfurylation and a novel NHC-promoted intramolecular cross-benzoin condensation reaction.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560432.
- Supporting Information (PDF) (opens in new window)
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For examples on the intramolecular cross-benzoin reaction between aldehydes and ketones, see:
For dasycarpuside A, see: