Synlett 2019; 30(01): 99-103
DOI: 10.1055/s-0037-1610324
letter
© Georg Thieme Verlag Stuttgart · New York

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

Shinichi Koguchi*
Department of Chemistry, School of Science, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa 259-1292, Japan   Email: koguchi@tokai-u.jp
,
Yuga Shibuya
,
Yusuke Igarashi
,
Haruka Takemura
› Author Affiliations
This work was supported by Tokai University General Research Organization Grant.
Further Information

Publication History

Received: 28 August 2018

Accepted after revision: 15 October 2018

Publication Date:
15 November 2018 (online)

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.

Supporting Information

 
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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%); Rf  = 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.