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Synlett 2011(20): 3023-3025  
DOI: 10.1055/s-0031-1289881
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Dibenzofurans by Palladium-Catalysed Tandem Denitrification/C-H Activation

Zhenting Du*, Jing Zhou, Changmei Si, Weili Ma
College of Science, Northwest A&F University, Yangling, Shaanxi, 712100, P. R. of China
Fax: +86(29)87092226; e-Mail: duzt@nwsuaf.edu.cn;
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Publication History

Received 30 August 2011
Publication Date:
11 November 2011 (online)

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Synthesis of Dibenzofurans by Palladium-Catalysed Tandem Denitrification/C–H ActivationSynlett 2012; 23(14): 2146-2146
DOI: 10.1055/s-0032-1317174

Abstract

A palladium-catalysed method for intramolecular cyclisation of ortho-diazonium salts of diaryl ethers to give dibenzofurans is described. The protocol uses 3 mol% palladium acetate as the catalyst in refluxing ethanol in the absence of base.

Key words

palladium acetate - dibenzofurans - diazonium salts

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17

CCDC 847585 contains the crystallographic data for this paper. These have been deposited with the Cambridge Crystallographic Data Center.

20

General procedure for the preparation of dibenzofurans from ortho-diazonium salts of diaryl ethers using Pd(OAc)2: To a stirred suspension of the ortho-diazonium salt of the appropriate diaryl ether (5 mmol) in EtOH (20 mL), a catalytic amount Pd(OAc)2 (33 mg, 0.15 mmol) was added, and the resulting mixture was heated at reflux for 30-60 min. The precipitate of metal was filtered, the filtrate was evaporated under vacuum, and the crude product was purified by column chromatography on silica gel eluting with a mixture of petroleum ether and EtOAc to give dibenzofurans.

21

Spectral data of compound 2i: ¹H NMR (500 MHz, CDCl3): δ = 7.88 (s, 1 H), 7.53 (d, J = 8.7 Hz, 1 H), 7.48 (d, J = 7.6 Hz, 1 H), 7.41 (d, J = 8.5 Hz, 1 H), 7.28 (t, J = 7.8 Hz, 1 H), 7.01 (δ, J = 7.6 Hz, 1 H), 4.07 (s, 3 H). ¹³C NMR (125 MHz, CDCl3): d = 154.4, 145.9, 145.6, 128.3, 127.2, 125.8, 124.8, 123.8, 120.6, 112.9, 112.8, 109.9, 56.2. IR: 1443, 1296, 1258, 1199, 1105 cm-¹.