Synthesis 2016; 48(12): 1865-1871
DOI: 10.1055/s-0035-1560432
special topic
© Georg Thieme Verlag Stuttgart · New York

Furans to Benzofurans: Intramolecular Cross-Benzoin Reactions Catalysed by N-Heterocyclic Carbenes

Rajendra P. Shirke
,
Virsinha Reddy
,
R. Vijaya Anand
,
S. S. V. Ramasastry*
Further Information

Publication History

Received: 24 February 2016

Accepted after revision: 08 March 2016

Publication Date:
15 April 2016 (eFirst)

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

 
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