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Synlett 2016; 27(09): 1408-1412
DOI: 10.1055/s-0035-1561382
DOI: 10.1055/s-0035-1561382
letter
Copper-Catalyzed Imino C–N Bond Formation with Aryl Boronic Acids under Aerobic Conditions
Further Information
Publication History
Received: 17 October 2015
Accepted after revision: 18 January 2016
Publication Date:
18 February 2016 (online)
Abstract
A copper-catalyzed, ligand- and base-free C–N cross-coupling reaction of iminochromenes with arylboronic acids in a nontoxic ethanol solvent at room temperature under air is developed. The product yields are found to be good to moderate. The conservation of the sensitive imine functional group implies the mildness of this protocol
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561382.
- Supporting Information
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References and Notes
- 1 Also called iminocoumarins.
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- 16 General Procedure for the Copper-Catalyzed Coupling of Iminochromene with Arylboronic Acids To a round-bottomed flask equipped with a stir bar, the iminochromene (1 mmol), Cu(OAc)2·H2O (20 mol%), and arylboronic acid (2.3 mmol) were added. EtOH (5 mL) was added, and the reaction mixture was stirred for 24 h at r.t. After completion of the reaction as monitored by TLC, the organic phase was concentrated under reduced pressure, and the solid residue was fractioned in EtOAc (20 mL) and H2O (10 mL) thrice. The organic phase was separated and dried on anhydrous Na2SO4. The solvent was removed in vacuum, and the crude residue was purified by column chromatography with EtOAc–PE to afford the respective N-arylated chromene. Physical and spectroscopic data given below are for compound 3a and may be taken as representative. For further details, see the Supporting Information. (Z)-N-3-Diphenyl-2H-chromen-2-imine (3a) Yellow solid (249 mg, 93% yield); mp 112–113 °C. IR (KBr): ν = 1737, 1643, 1587, 1485, 1365, 1230, 1116 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.79–7.72 (m, 2 H), 7.46–7.30 (m, 7 H), 7.29 (s, 1 H), 7.20–7.13 (m, 2 H), 7.13–7.05 (m, 1 H), 7.02 (d, J = 8.2 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 152.9, 148.9, 146.6, 136.7, 133.6, 133.3, 132.1, 130.1, 129.1, 128.7, 128.4, 128.3, 128.0, 127.2, 123.9, 123.4, 122.8, 122.5, 120.4, 115.6, 115.3. ESI-HRMS: m/z calcd for C21H16NO [M + H]+ : 298.1226; found: 298.1277.
- 17 See the Supporting Information.
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