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Synlett 2014; 25(20): 2895-2898
DOI: 10.1055/s-0034-1379472
DOI: 10.1055/s-0034-1379472
letter
Synthesis of Aryl- and Alkylquinones through Rhodium-Catalyzed C–C Coupling under Mild Conditions
Further Information
Publication History
Received: 17 July 2014
Accepted after revision: 15 September 2014
Publication Date:
21 October 2014 (online)
Abstract
A direct arylation, alkylation of quinones with aryl and alkyl boronic acids through rhodium-catalyzed C–C coupling has been developed under mild conditions. [Cp*RhCl2]2 was shown to be the most effective catalyst for the transformation. More importantly, good to excellent yields were obtained under room temperature and base-free conditions. This reaction provides a practical, efficient method for the synthesis of aryl- and alkylquinones.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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- 11 General Procedure for the Reaction of Benzoquinone with Boronic Acid To a solution of benzoquinone (0.5 mmol, 1.0 equiv) and [Cp*RhCl2]2 (0.025 mmol, 5 mol%) in CH2Cl2 (2 mL) was added the boronic acid (0.75 mmol, 1.5 equiv), H2O (1 mL). Then the solution was stirred vigorously at r.t. for 10 h. Upon completion, the reaction was diluted with CH2Cl2 (3 mL) and washed with 5% NaHCO3. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3 × 4 mL), dried over Na2SO4, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (EtOAc–PE, 1:10) to provide the corresponding product 2-p-tolyl[1,4]benzoquinone (3b). 1H NMR (400 MHz, CDCl3): δ = 7.39 (d, J = 8.2 Hz, 2 H), 7.26 (d, J = 8.0 Hz, 2 H), 6.88–6.77 (m, 3 H), 2.40 (s, 3 H).