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Synlett 2017; 28(05): 601-606
DOI: 10.1055/s-0036-1588361
DOI: 10.1055/s-0036-1588361
letter
Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids
Further Information
Publication History
Received: 19 August 2016
Accepted after revision: 30 October 2016
Publication Date:
17 November 2016 (online)
Abstract
A rapid, ligand-free, base-accelerated, copper-catalyzed homocoupling reaction of (het)arylboronic acids is presented. A CuCl2·2H2O/Na2CO3-based catalyst enabled the formation of bi(het)aryl compounds by a homocoupling process in moderate to excellent yields (72–97%) within 15 minutes. A mechanism for the copper-catalyzed base-accelerated reaction is proposed.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588361.
- Supporting Information
-
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- 22 Bi(het)aryls 2a–t; General Procedure A vial was charged with the appropriate (het)arylboronic acid (0.3 mmol), CuCl2·2H2O (2.5 mg, 5 mol%), Na2CO3 (10 mol%), and MeOH (1 mL), and the mixture was stirred at 25 °C in the air for 5–15 min while the reaction was monitored by TLC. The reaction was then quenched with two drops of H2O. The mixture was then diluted with EtOAc (2 mL) and filtered through a pad of MgSO4 and silica. The pad was rinsed with additional EtOAc, and the solution was concentrated in vacuum. The crude material was purified by flash chromatography (silica gel). 4,4′-Di-tert-butylbiphenyl (2a) Prepared by following the general procedure with (4-tert-butylphenyl)boronic acid (53.4 mg, 0.3 mmol) for 15 min at r.t. Purification by flash chromatography (silica gel, PE) gave a white solid; yield: 37.9 mg (95%); mp 126–127 °C. 1H NMR (400 MHz, CDCl3): δ = 7.57 (d, J = 8.4 Hz, 4 H), 7.49 (d, J = 8.4 Hz, 4 H), 1.40 (s, 18 H). 13C{1H} NMR (100 MHz, CDCl3): δ = 149.9, 138.2, 126.6, 125.6, 34.5, 31.4.