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Volumn , Issue 6, 2008, Pages 849-852

Copper-catalyzed addition of halide and sulfide groups to alkynes utilizing disulfides with tetrabutylammonium halides

Author keywords

Alkenyl halides; Alkenyl sulfides; Copper catalyst; Disulfides; Internal alkynes

Indexed keywords

ALKYNE; COPPER; DISULFIDE; HALIDE; SULFIDE; TETRABUTYLAMMONIUM HALIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; STRUCTURE ACTIVITY RELATION;

EID: 42049083143 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042903 Document Type: Article

Times cited : (35)

References (25)

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17
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- Typical Procedure: To a mixture of CuI (1.9 mg, 0.01 mmol, bpy (1.6 mg, 0.01 mmol, diphenyl disulfide (21.8 mg, 0.1 mmol, and TBAB (70.9 mg, 0.22 mmol) in AcOH (0.3 mL) was added 4-octyne (22.0 mg, 0.2 mmol, and the mixture was stirred at 100°C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and sat. NaCl and dried over anhyd MgSO4. Chromatography on silica gel(hexane) gave (E)-4-bromo-5-phenylthiooctene (48.7 mg, 81, E)-n-Pr(PhS)C=C(Br)n-Pr: IR (neat, 2960, 2870, 1582, 1476, 1461 cm-1. 1NMR (270 MHz, CDCl3, δ, 7.16-7.31 (m, 5 H, 2.90 (t, J, 7.5 Hz, 2 H, 2.38 (t, J, 7.5 Hz, 2 H, 1.51-1.67 (m, 4 H, 0.92 (t, J, 7.5 Hz, 3 H, 0.86 (t, J, 7.5 Hz, 3 H, 13C NMR 67.5 MHz, CDCl3, δ, 135.3, 132.8, 131.5, 129.2, 128.9, 126.2, 41.2, 38
- 19SI: C, 48.56; H, 5.53. Found: C, 48.48; H, 5.47.

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19
- 42049083557
- 20SBr: C, 76.30; H, 9.15. Found: C, 76.03; H, 8.92.
- 20SBr: C, 76.30; H, 9.15. Found: C, 76.03; H, 8.92.

20
- 42049121945
- In the absence of bpy, the yield of 3 was 39% yield
- In the absence of bpy, the yield of 3 was 39% yield.

21
- 42049108892
- E)-n-Pr(4-MeC6H 4S)C=C(Br)n-Pr: IR (neat, 2960, 2929, 1894, 1602, 1491 cm-1. 1H NMR (270 MHz, CDCl3, δ, 7.15 (d, J, 8.3 Hz, 2 H, 7.09 (d, J, 8.3 Hz, 2 H, 2.90 (t, J, 7.4 Hz, 2 H, 2.34 (t, J, 7.4 Hz, 2 H, 2.32 (s, 3 H, 1.49-1.67 (m, 4 H, 0.93 (t, J, 7.4 Hz, 3 H, 0.86 (t, J, 7.4 Hz, 3 H, 13C NMR (67.5 MHz, CDCl3, δ, 136.5, 132.2, 131.5, 131.4, 130.1, 129.8, 41.2, 38.5, 21.9, 21.0, 13.6, 13.1. Anal. Calcd for C15H21SBr: C, 57.50; H, 6.76. Found: C, 57.21; H, 6.67, E)-n-Pr(4-MeOC6H 4S)C=C(Br)n-Pr: IR (neat, 2960, 2930, 1592, 1493 cm-1. 1H NMR (270 MHz, CDCl3, δ, 7.24 (d, J, 8.9 Hz, 2 H, 6.84 (d, J, 8.9 Hz, 2 H, 3.79 s, 3 H, 2.91
- 2SBr: C, 56.21; H, 4.16. Found: C, 56.32; H, 4.25.

22
- 42049119186
- The stereochemistry of compounds in entries 12 and 14 was determined by NOE after the debromination.
- The stereochemistry of compounds in entries 12 and 14 was determined by NOE after the debromination.

23
- 0342826474
- For the preparation of PhSCu, see:, John Wiley & Sons: New York
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- Adams, R.¹ Reifschneider, W.² Ferretti, A.³

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