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Synlett 2012; 23(7): 1074-1078
DOI: 10.1055/s-0031-1290526
DOI: 10.1055/s-0031-1290526
letter
Unexpected Base-Promoted Synthesis of Tetrasubstituted Furans via Palladium-Catalyzed Oxidation and Cyclization of Carbon–Carbon Triple Bond with Molecular Oxygen
Further Information
Publication History
Received: 05 January 2012
Accepted after revision: 14 February 2012
Publication Date:
29 March 2012 (online)
Abstract
A new approach to the synthesis of tetrasubstituted furans using aromatic alkynes catalyzed by PdCl2 in DMA (N,N-dimethylacetamide)–H2O with dioxygen as the sole oxidant is described, in which the oxygen atom of the furan was from water. The preliminary mechanistic understanding of this transformation was investigated.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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- 8 Typical Procedure for Substrate 1a: The reaction was carried out in a 150-mL Teflon-lined 316-L stainless steel autoclave and a magnetic stirrer. A mixture of PdCl2 (5 mol%, 0.025 mmol, 4.4 mg), NaOAc (5 mol%, 0.025 mmol, 2.1 mg), 1a (0.5 mmol, 89 mg), H2O (0.1 mL) and DMA (2 mL) was placed in the 150-mL Teflon-lined 316-L stainless steel autoclave. Then, 0.1 MPa of O2 was introduced. The mixture was stirred for 6 h at 80 °C. After the reaction, the reactor was quickly cooled to r.t. The excess of O2 was depressurized slowly. The products were extracted using a Et2O–H2O mixture (1:1; 3 × 20 mL). The Et2O layers containing the products were dried over Na2SO4, filtrated and concentrated under reduced pressure. The resultant crude mixture was purified by column chromatography (silica gel) with a mixture of EtOAc–hexane (1:20) as eluent to afford 2a (70 mg, yield 76%). The product was characterized by NMR and confirmed by comparison with the reported authentic NMR data