Organoselenosilane-Mediated Selective Mild Access to Selenolesters, Selenoanhydrides and Diacyl Diselenides

Abstract

Reaction of acyl chlorides with phenylselenotrimethyl­silane promoted by TBAF afforded a mild general access to selenolesters in good yields. When acyl chlorides were reacted with bis(trimethylsilyl)selenide (HMDSS) in 2:1 or 1:1 ratio a selective entry to selenoanhydrides or diacyl diselenides respectively was obtained.

Key words

selenosilanes - selenolesters - diacyl selenides - diacyl diselenides - fluoride ion

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25

Preparation of Se-Phenyl 2-chloropropaneselenoate (3f): To a solution of 2-chloropropanoyl chloride (30 mg, 0.24 mmol) in anhyd THF (0.5 mL) was added under an inert atmosphere phenylselenotrimethylsilane (71 µL, 0.28 mmol). TBAF (50 µL, 1 M THF solution, 0.05 mmol) was added dropwise at 0 ˚C. The reaction was warmed to r.t. and stirred overnight. The mixture was then extracted with Et₂O, washed with brine and dried over Na₂SO₄. Filtration and evaporation of the solvent gave the crude 3f as a yellow oil, which was purified by TLC on silica gel (n-hexane-CH₂Cl₂, 2:1). Yield: 63%. ^¹H NMR (200 MHz, CDCl₃): δ = 1.75 (d, 3 H, J = 7.0 Hz), 4.58 (q, 1 H, J = 7.0 Hz), 7.43-7.46 (m, 3 H), 7.51-7.55 (m, 2 H). ^¹³C NMR (50 MHz, CDCl₃): δ = 22.1, 63.7, 127.5, 129.3, 130.6, 131.3, 200.4. ⁷⁷Se (38 MHz, CDCl₃): δ = 650.6. MS: m/z (%) = 248 (26) [M⁺], 192 (22), 158 (39), 91 (44), 78 (55), 63 (100).

30

Synthesis of 4-Methoxybenzoic Selenoanhydride (5c): A solution of 4-methoxybenzoyl chloride (24 µL, 0.18 mmol) and TBAF (1 M in THF, 18 µL, 0.018 mmol) in anhyd THF (0.5 mL) was cooled under atmosphere at 0 ˚C, and treated dropwise with bis(trimethylsilyl)selenide (HMDSS; 21 mg, 0.09 mmol). The red mixture turned to pale yellow after few minutes. After warming to r.t., and stirring for 2 h, the solution was diluted with Et₂O, washed with brine and dried over Na₂SO₄. The crude product was purified by flash column chromatography (n-hexane-CH₂Cl₂, 1:1) to afford 5c as a yellow solid (24 mg, 75%). ^¹H NMR (200 MHz, CDCl₃): δ = 3.88 (s, 6 H), 6.93-6.98 (m, 4 H), 7.92-7.96 (m, 4 H). ^¹³C NMR (50 MHz, CDCl₃): δ = 55.6, 114.1, 130.9, 131.5, 164.5, 185.9. ⁷⁷Se (38 MHz, CDCl₃): δ = 730.0.

31

Preparation of 4-Methoxybenzoic Diselenoperoxy-anhydride (6c): A solution of 4-methoxybenzoyl chloride (24 µL, 0.18 mmol) in anhyd THF (0.5 mL) was added under an inert atmosphere with HMDSS (44 mg, 0.19 mmol) and it was cooled to 0 ˚C. TBAF (1 M in THF, 38 µL, 0.038 mmol) was then added dropwise. The red mixture so formed was warmed to r.t. and stirred for 2 h. Upon quenching with brine, the red solution turned slowly to pale yellow. Extraction with Et₂O, drying over Na₂SO₄ and removal of the solvent under vacuum afforded the crude product, which was purified by flash column chromatography (n-hexane-CH₂Cl₂, 1:1) to produce 6c as a yellow solid (55 mg, 71%). ^¹H NMR (200 MHz, CDCl₃):
δ = 3.88 (s, 6 H), 6.92-6.98 (m, 4 H), 7.91-8.07 (m, 4 H). ^¹³C NMR (50 MHz, CDCl₃): δ = 55.6, 114.2, 129.3, 130.5, 164.4, 186.9. ⁷⁷Se (38 MHz, CDCl₃): δ = 598.5.