Palladium-Catalyzed Direct Arylation Reaction of 2,3,5-Trisubstituted Furans with Aryl Iodides or Aryl Bromides

Abstract

Pd-catalyzed direct arylation of 2,3,5-trisubstituted furans with a variety of aryl iodides or aryl bromides that showed high activity with reasonably broad scope was developed. Under optimal conditions, all reactions gave the desired products in moderate to good yields.

Key words

palladium - arylation reaction - 2,3,5-trisubstituted furans - aryl iodides - aryl bromides

References and Notes

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14

General Procedure for the Synthesis of 1a
Diethyl acetylenedicarboxylate (2 mmol), prop-2-yn-1-ol (2 mmol), DABCO (0.2 mmol) in CH₂Cl₂ were stirred for 10 min at r.t. And then the solution was evaporated to dryness under reduced pressure. Subsequently, CuI (10% mmol) and DMF were added at 80 ˚C. After completion of the reaction (monitored by TLC), the solution was evaporated to dryness under reduced pressure, and then H₂O (10 mL) was added. The aqueous solution was extracted with Et₂O (3 × 10 mL), and the combined extract was dried with anhyd MgSO₄. The solvent was removed, and the crude product was separated by column chromatography to give a pure sample of 1a.

15

General Procedure for the Synthesis of 1c
Diethyl acetylenedicarboxylate (2 mmol), prop-2-yn-1-ol (2 mmol), DABCO (0.2 mmol) in CH₂Cl₂ were stirred for 10 min at r.t. And then the solution was evaporated to dryness under reduced pressure. Subsequently, AgOAc/Ph₃P and toluene were added at 50 ˚C. After completion of the reaction (monitored by TLC), the solution was evaporated
to dryness under reduced pressure, and then H₂O (10 mL) was added. The aqueous solution was extracted with Et₂O (3 × 10 mL), and the combined extract was dried with anhyd MgSO₄. The solvent was removed, and the crude product was separated by column chromatography to give a pure sample of 1c.

16

General Procedure for the Synthesis of 3a
To the mixture of Pd(OAc)₂ (5% mol), Ph₃P (10% mol), Cs₂CO₃ (1.0 mmol), 1a (0.5 mmol), 2a (0.7 mmol), and DMP (4 mL) were added successively. The mixture was stirred at 120 ˚C for 20 hours. The solution was extracted with EtOAc (3 × 15 mL), and the combined extract was dried with anhyd MgSO₄. Solvent was removed, and the residue was separated by column chromatography to give the pure sample 3a.
Diethyl 5-Formyl-4-phenylfuran-2,3-dicarboxylate (3a)
^¹H NMR (400 MHz, CDCl₃): δ = 9.70 (s, 1 H), 7.47 (s, 5 H), 4.43 (q, J = 8.0 Hz, 2 H), 4.28 (q, J = 8.0 Hz, 2 H), 1.40 (t, J = 8.0 Hz, 3 H), 1.22 (q, J = 8.0 Hz, 3 H). ^¹³C NMR (100 MHz, CDCl₃): δ = 178.0, 162.0, 157.1, 147.5, 144.3, 136.1, 129.7, 129.5, 128.7, 127.5, 126.3, 62.3, 62.1, 14.0, 13.7.
MS (EI): m/z (%) = 316, 288, 225, 213, 170, 115, 77.