C–Te Cross-Coupling of Diaryl Ditellurides with Arylboronic Acids by Using Copper(I) Thiophene-2-carboxylate under Mild Conditions

Abstract

We describe the successful cross-coupling of diaryl ditellurides with arylboronic acids by using copper(I) thiophene-2-carboxylate (CuTC) under mild conditions. Although other studies have reported that highly polar solvents (such as DMSO) or bases are required, this reaction was completed by using CuTC and common solvents under neutral conditions at room temperature. This cross-coupling reaction was performed with diaryl ditellurides and arylboronic acids bearing various groups, affording the corresponding diaryl tellurides in good to excellent yields.

Key words

C–Te coupling - copper catalysis - diaryl ditellurides - aryl­boronic acids - diaryl tellurides

• References and Notes

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• 8 Diaryl Tellurides 1–10; General Procedure The appropriate diaryl ditelluride (0.5 mmol) and arylboronic acid (1.2 mmol) were stirred in CH₂Cl₂ (3 ml) at r.t. for 30 min. CuTC (1.2 mmol) was then added and the mixture was stirred at r.t. for 24 h. The mixture was concentrated, and the product was purified by column chromatography. 1-Phenyl-4-(phenyltelluro)benzene (1) Yellow oil; yield: 274.5 mg (0.93 mmol; 94%); R_f  = 0.35 (hexane). ¹H NMR (500 MHz, CDCl₃): δ = 2.25 (s, 3 H), 6.95–7.56 (m, 9 H). ¹³C NMR (125 MHz, CDCl₃): δ = 21.3, 110.3, 115.3, 127.6, 129.5 (2 C), 130.5 (2 C), 137.3 (2 C), 138.1, 138.8 (2 C). HRMS (APCI): m/z [M + H]⁺ calcd for C₁₃H₁₃Te: 299.0079; found: 299.02484.