Iodine-Mediated Sulfenylation of Imidazo[1,2-a]pyridines with Ethyl Arylsulfinates

Jian Sun; Yangxiu Mu; Zafar Iqbal; Jing Hou; Minghua Yang; Zhixiang Yang; Dong Tang

doi:10.1055/a-1396-5933

Synlett, Table of Contents

Synlett 2021; 32(10): 1014-1018
DOI: 10.1055/a-1396-5933

letter

Iodine-Mediated Sulfenylation of Imidazo[1,2-a]pyridines with Ethyl Arylsulfinates

Jian Sun

^aNingxia Center of Agricultural Organic Synthesis, Agricultural Resource and Environment Institute of Ningxia Academy of Agriculture and Forestry Science, Yinchuan, 750002, P. R. of China

,

Yangxiu Mu

^aNingxia Center of Agricultural Organic Synthesis, Agricultural Resource and Environment Institute of Ningxia Academy of Agriculture and Forestry Science, Yinchuan, 750002, P. R. of China

,

Zafar Iqbal

^aNingxia Center of Agricultural Organic Synthesis, Agricultural Resource and Environment Institute of Ningxia Academy of Agriculture and Forestry Science, Yinchuan, 750002, P. R. of China

,

Jing Hou

^aNingxia Center of Agricultural Organic Synthesis, Agricultural Resource and Environment Institute of Ningxia Academy of Agriculture and Forestry Science, Yinchuan, 750002, P. R. of China

,

Minghua Yang

^bDepartment of Chemistry, Lishui University, Lishui, 323000, P. R. of China

,

Zhixiang Yang

^aNingxia Center of Agricultural Organic Synthesis, Agricultural Resource and Environment Institute of Ningxia Academy of Agriculture and Forestry Science, Yinchuan, 750002, P. R. of China

,

Dong Tang∗

^aNingxia Center of Agricultural Organic Synthesis, Agricultural Resource and Environment Institute of Ningxia Academy of Agriculture and Forestry Science, Yinchuan, 750002, P. R. of China

^bDepartment of Chemistry, Lishui University, Lishui, 323000, P. R. of China

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Abstract

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Abstract

A simple iodine-mediated approach is reported for the synthesis of sulfenylated imidazo[1,2-a]pyridines through the reaction of imidazo[1,2-a]pyridines with ethyl arylsulfinates under mild conditions. The reaction scope was investigated, and a plausible mechanism is proposed to elucidate the reaction process and activation mode. The results indicate that ethyl sulfinates are efficient sulfur sources for the construction of C–S bonds.

Key words

iodine - ethyl arylsulfinates - sulfenylation - imidazopyridines - arylsulfenylation

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References

References and Notes

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22 3-(Arylsulfanyl)imidazo[1,2-a]pyridines 3aa–am and 3ba–ka; General Procedure A sealed tube was charged with the appropriate ethyl arylsulfinate (0.4 mmol), imidazo[1,2-a]pyridine (0.2 mmol), I₂ (0.75 equiv), and MeCN (2 mL), and the mixture was stirred at 120 °C for 6 h. When the reaction was complete, the mixture was allowed to cool to r.t. and concentrated under reduced pressure. The residue was purified by chromatography (silica gel, 10% EtOAc–PE). 3-[(4-Methylphenyl)sulfanyl]-2-phenylimidazo[1,2-a]pyridine (3aa) Yellow solid; yield: 45 mg (72%); mp 131–133 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.30 – 8.14 (m, 3 H), 7.72 (d, J = 9.0 Hz, 1 H), 7.49–7.25 (m, 4 H), 7.01 (d, J = 8.0 Hz, 2 H), 6.95–6.78 (m, 3 H), 2.24 (s, 3 H). ¹³C NMR (101 MHz, CDCl₃): δ = 151.21, 147.04, 136.05, 133.42, 131.51, 130.23, 128.58, 128.43, 128.41, 126.61, 125.84, 124.55, 117.64, 113.04, 106.89, 20.91. HRMS (ESI): m/z [M + H]⁺ calcd for C₂₀H₁₇N₂S: 317.1107; found: 317.1105.

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