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Synlett 2016; 27(20): 2815-2818
DOI: 10.1055/s-0036-1589214
DOI: 10.1055/s-0036-1589214
letter
Iodine-Promoted Metal-Free Head-to-Tail Dimerization of Styrenes Affording 1,3-Diarylbut-1-enes
Weitere Informationen
Publikationsverlauf
Received: 02. Juli 2016
Accepted after revision: 21. August 2016
Publikationsdatum:
12. September 2016 (online)
Abstract
A convenient and efficient iodine-mediated head-to-tail dimerization of styrenes to produce the corresponding dimers in the presence of triethyl phosphite is reported. The advantages of the present protocol are metal-free conditions, short reaction time, simplicity, and high efficiency.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589214.
- Supporting Information
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References and Notes
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- 10 Typical Experimental Procedure for the Synthesis of Compound 2a P(OEt)3 (0.20 mmol, 33.2 mg) was added to a solution of 1a (0.20 mmol, 20.8 mg) and I2 (0.40 mmol, 101.2 mg) in DCE (1 mL), and the reaction mixture was stirred under reflux conditions for 5–30 min. After completion of the reaction, the reaction mixture was diluted with EtOAc, and quenched with sat. Na2S2O3 solution and extracted twice with EtOAc (3 × 15 mL). The organic layer was washed with H2O and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo, and the residue was subjected to column chromatography using EtOAc in PE as the eluent to afford the target compound 2a. (E)-But-1-ene-1,3-diyldibenzene (2a)6a Colorless oil; yield: 16.2 mg (78%). 1H NMR (400 MHz, CDCl3): δ = 7.37–7.18 (m, 10 H), 6.41 (d, J = 4.0 Hz, 2 H), 3.66–3.63 (m, 1 H), 1.47 (d, J = 8.0 Hz, 3 H). 1,1,3-Trimethyl-3-phenyl-2,3-dihydro-1H-indene (2m)6h Colorless oil; yield: 18.4 mg (78%). 1H NMR (400 MHz, CDCl3): δ = 7.28–7.11 (m, 9 H), 2.43 (d, J = 12.0 Hz, 1 H), 2.20 (d, J = 12.0 Hz, 1 H), 1.69 (s, 3 H), 1.35 (s, 3 H), 1.03 (s, 3 H).