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Volumn , Issue 13, 2007, Pages 2081-2085

Preparation of polyfunctional aryl triazenes via a direct insertion reaction of Zn in the presence of LiCl

Author keywords

Copper catalysis; Functionalized triazenes; Lithium chloride; Negishi cross coupling; Zinc insertion

Indexed keywords

LITHIUM CHLORIDE; POLYFUNCTIONAL GROUP; TRIAZENE DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION;

EID: 34548161442 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984905 Document Type: Article

Times cited : (11)

References (16)

1
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4
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5
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6
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- Nicolaou, K.C.¹ Li, H.² Boddy, C.N.C.³ Ramanjulu, J.M.⁴ Yue, T.Y.⁵ Natarajan, S.⁶ Chu, X.J.⁷ Bräse, S.⁸ Rübsam, F.⁹

9
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10
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12
- 34548151521
- Typical Procedure: Preparation of the Aryl Triazene 3b Anhydrous LiCl (8 mmol) was placed in an Ar-flushed flask and dried for 5 min at 130°C under vacuum (1 mbar, Zinc dust (8 mmol, 2.0 equiv, <10 micron, 98, Aldrich) was added under Ar and the mixture was dried again for 10 min at 130°C under vacuum (1 mbar, The reaction flask was evacuated and refilled with Ar twice. Then THF (4 mL) was added and the zinc dust was activated with BrCH2CH2Br (5 mol, and Me3SiCl (2 mol, by warming the reaction mixture with a heat gun for a few minutes. 1-(2-Carbethoxy-4-iodophenylazo)pyrrolidine (2a, 1.5 g, 4 mmol) was added neat at r.t. and the reaction mixture was gradually heated to 50°C. The insertion reaction was complete after 7 h (checked by GC analysis of reaction aliquots, the conversion was ca. 92, Titration of an aliquot (1 mL) of the organozinc reagent with iodine indicated that the concentration of 1a was ca. 0.88
- +.

13
- 34548155436
- Aryl Triazene 3d Mp 73.8-76.7°C 1H NMR (600 MHz, CDCl3, 25°C, δ, 9.97 (s, 1 H, 8.01 (d, J, 7.9 Hz, 1 H, 7.61-7.66 (m, 2 H, 7.60 (s, 1 H, 7.44 (d, J, 8.2 Hz, 1 H, 7.40 (d, J, 7.9 Hz, 1 H, 7.21 (t, J, 8.2 Hz, 1 H, 3.95-4.01 (m, 2 H, 3.75-3.82 (m, 2 H, 2.00-2.12 (m. 4 H) ppm. 13C NMR (150 MHz, CDCl3, 25°C, δ, 191.6, 153.6, 143.6, 134.8, 134.1, 133.9, 133.8, 133.6, 130.6, 128.3, 128.1, 117.6, 117.3, 107.4, 51.5. 47.3, 23.9, 23.4 ppm. MS (70 eV, EI, m/z, 304 (43, M, 234 (72, 206 (100, 177 (42, 151 (41, IR (KBr, v, 3057 (w, 2973 (w, 2873 (w, 2748 (w, 2223 (m, 1689 (s, 1596 (m, 1470 (m, 1384 (s, 1307 (s, 1267 (s, 1098 (m, 903 (w) cm-1. HRMS EI, m/z calcd for C 18H16N4O: 304.1324; found: 304.1328
- 4O: 304.1324; found: 304.1328.

14
- 34548161381
- Aryl Triazene 3e Mp 120.3-122.2°C 1H NMR (600 MHz, CDCl3, 25°C, δ, 7.60 (s, 1 H, 7.51 (d, J, 8.4 Hz, 1 H, 7.48 (d, J, 8.4 Hz, 1 H, 7.43 (d, J, 8.6 Hz, 2 H, 6.90 (d, J, 8.6 Hz, 2 H, 3.92 (br s, 2 H, 3.83 (s, 3 H, 3.49 (br s, 2 H, 1.95-2.00 (m, 4 H) ppm. 13C NMR (150 MHz, CDCl3, 25°C, δ, 158.9, 151.5, 136.3, 134.2, 131.3. 131.0, 130.5, 119.6, 117.9, 113.0, 107.7, 55.2, 51.1, 46.9, 23.9, 23.3 ppm. MS (70 eV, EI, m/z, 306 (22, M, 236 (11, 208 (100, 193 (32, 177 (6, 165 (19, IR (KBr, v, 2948 (w, 2879 (w, 2830 (w, 2215 (s, 1595 (m, 1513 (m, 1479 (m, 1383 (s, 1243 (s, 1173 (s, 1030 (m) cm-1. HRMS EI, m/z calcd for C18H18N4O: 306.1481; found: 306.1483
- 4O: 306.1481; found: 306.1483.

15
- 34548181552
- 10INO: 346.9807; found: 346.9789.
- 10INO: 346.9807; found: 346.9789.

16
- 34548173677
- Aryl Triazene 7 Mp 151.4-152.6°C. 1HNMR (600 MHz, CDCl3, 25°C, δ, 7.38 (d, J, 8.4 Hz, 2 H, 7.32-7.36 (m, 4 H, 3.88 (br s, 2 H, 3.78 (br s, 2 H, 3.48 (br s, 2 H, 2.34 (s, 3 H, 1.98-2.03 (m, 4 H, 1.92-1.97 (m, 4 H) ppm. 13C NMR (150 MHz, CDCl3, 25°C, δ, 150.3, 149.3, 136.5, 135.5, 135.4, 134.4, 133.0, 130.6, 119.5, 119.3, 103.7, 50.8, 46.6, 23.9, 23.8, 23.4, 20.6 ppm. MS (70 eV, EI, m/z, 387 (100, M, 348 (11, 289 (59, 277 (53, 262 (49, 219 (65, 205 (12, 191 (72, 165 (13, 152 (25, 116 (10, 70 (19, IR (KBr, v, 3051 (w, 2974 (w, 2874 (w, 2210 (w)1596 (w, 1397 (s, 1340 (s, 1312 (m, 1218 (m, 1148 (m, 970 (w) cm-1. HRMS EI, m/z calcd for C22H25N7: 387.2171; found: 387.2174
- 7: 387.2171; found: 387.2174.

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