Metal-Free, DTBP-Mediated Methylthiolation of Arylboronic Acids with Dimethyldisulfide

Xiang-mei Wu; Jia-ming Lou; Guo-bing Yan

doi:10.1055/s-0035-1562499

Synlett, Table of Contents

Synlett 2016; 27(15): 2269-2273
DOI: 10.1055/s-0035-1562499

letter

Metal-Free, DTBP-Mediated Methylthiolation of Arylboronic Acids with Dimethyldisulfide

Xiang-mei Wu*

Department of Chemistry, Lishui University, Lishui, Zhejiang 323000, P. R. of China Email: lswxm7162@163.com Email: gbyan@lsu.edu.cn

,

Jia-ming Lou

Department of Chemistry, Lishui University, Lishui, Zhejiang 323000, P. R. of China Email: lswxm7162@163.com Email: gbyan@lsu.edu.cn

,

Guo-bing Yan*

Department of Chemistry, Lishui University, Lishui, Zhejiang 323000, P. R. of China Email: lswxm7162@163.com Email: gbyan@lsu.edu.cn

› Author Affiliations

Abstract

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Abstract

An efficient method for the C–S bond formation via the coupling reaction of arylboronic acids with dimethyldisulfide has been developed under the metal-free conditions. This novel protocol provides an attractive route for the synthesis of aryl methyl sulfides, due to its operational simplicity, satisfactory yields, excellent functional-group tolerance, as well as the mild reaction conditions.

Key words

methylthiolation - arylboronic acids - dimethyldisulfide - aryl methyl sulfides - di-tert-butyl peroxide

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References and Notes

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22 General Procedure Arylboronic acid (1.0 mmol), dimethyldisulfide (2.0 mmol), DTBP (3.0 mmol), and MeCN (2.0 mL) were taken in a sealed tube. The reaction mixture was stirred at 120 °C for 12 h in air. After cooling to room temperature, the product was diluted with H₂O (5 mL) and extracted with EtOAc (4 × 10 mL). The extracts were combined and washed by brine (3 × 10 mL), dried over MgSO₄, filtered, and evaporated, and purified by chromatography on silica gel to obtain the desired products with EtOAc–hexane (1:30 to 1:100 v/v). The products were characterized by their spectral and analytical data and compared with those of the known compounds (see Supporting Information). Typical Data for Representative Compound 4-Methylthioanisole (Table 2, Entry 2) Colorless oil. ¹H NMR (300 MHz, CDCl₃): δ = 7.17–7.14 (d, J = 8.1 Hz, 2 H), 7.08–7.05 (d, J = 8.1 Hz, 2 H), 2.42 (s, 3 H), 2.28 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 135.0, 134.8, 129.7, 127.3, 20.9, 16.5. GC-MS (EI): m/z = 138 [M⁺].

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Supplementary Material

Supporting Information