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Synlett 2015; 26(07): 975-979
DOI: 10.1055/s-0034-1380320
DOI: 10.1055/s-0034-1380320
letter
Synthesis of Symmetrical Biaryls through Palladium-Catalyzed Ligand-Free Homocoupling of Aryliodine(III) Diacetates
Authors
Further Information
Publication History
Received: 16 December 2014
Accepted after revision: 19 January 2015
Publication Date:
19 February 2015 (online)
Abstract
An efficient process for the synthesis of symmetrical biaryls from readily available and bench-stable aryliodine(III) diacetates has been developed with high regional selectivity. The process exhibited high selectivities and good functional group tolerance with respect to methyl, bromo, chloro and cyano groups. Mechanistic studies revealed that the transformation involved in situ generation of aryl iodide from heating-promoted degradation of aryliodine(III) diacetate, followed by Ullmann-type homocoupling.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380320.
- Supporting Information (PDF)
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- 14 General Procedure (Preparation of 2): A mixture of aryliodine(III) diacetate 1 (0.2 mmol), K2CO3 (110.6 mg, 0.8 mmol, 4 equiv), Pd(OAc)2 (4.5 mg, 0.02 mmol, 10 mol%) and DMF (2 mL) was stirred at 110 °C for 2 h. After cooling to r.t., the reaction mixtures were diluted with H2O (10 mL) and filtered through a pad of silica gel that was then washed with Et2O (3 × 10 mL). The combined organic phase was washed with brine (2 × 20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was then purified by flash chromatography on silica gel to provide the corresponding product. The product was characterized by GC–MS and NMR spectroscopy.