Reaction SMILES: [C:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)#[CH:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18]1[CH2:22]OC[CH2:19]1.CO>CCOCC>[N+:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[C:2][CH2:19][CH2:18][CH3:22])=[CH:8][CH:7]=1)([O-:11])=[O:10]
Reactant: C#Cc1ccc([N+](=O)[O-])cc1
Reactant: C1CCOC1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CO
Solvent: CCOCC
Product: CCCC#Cc1ccc([N+](=O)[O-])cc1
Reaction time: 2 h

Procedure:
TMS-protected 4a was obtained as a colorless, crystalline solid (279 mg, 99%); 1H NMR (300 MHz, CDCl3) δ 8.15 (d, J=8.7 Hz, 2H), 7.58 (d, J=9.0 Hz, 2H), 0.25 (s, 9H) ppm. 13C NMR (75 MHz, CDCl3) δ 146.9, 132.5, 129.8, 123.3, 102.5, 100.4, 85.7, −0.43 ppm. Deprotection was done by dissolving 4a (279 mg, 1.30 mmol) in 3:1 THF-MeOH (4 mL) and adding potassium carbonate (528 mg, 3.82 mmol) slowly. The reaction was stirred for 2 h, after which the mixture was diluted with Et2O, washed with saturated NH4Cl and H2O, dried with MgSO4 and concentrated under reduced pressure. The resultant terminal alkyne 4a (129 mg, 68%) was then used with no further purification. 1H-NMR (300 MHz, CDCl3) δ 8.19 (d, J=8.4 Hz, 2H), 7.64 (d, J=8.7 Hz, 2H), 3.36 (s, 1H) ppm. 13C NMR (75 MHz, CDCl3) δ 147.3, 132.8, 128.7, 123.4, 53.3 ppm. 1-Nitro-4-(1-pentynyl)benzene (4b) was obtained as a brown oil (148 mg, 65%); 1H-NMR (300 MHz, CDCl3) δ 8.15 (d, J=8.7 Hz, 2H), 7.52 (d, J=9.0 Hz, 2H), 2.42 (t, 2H), 1.68-1.61 (m, 2H), 1.05 (t, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ 132.1, 131.7, 131.1, 123.3, 96.4, 79.3, 21.7, 21.4, 13.4. ppm 1-(1-Hexynyl)-4-nitrobenzene (4c) was obtained as an amber oil (241 mg, 99%). 1H-NMR (300 MHz, CDCl3) δ 8.14 (d, J=9.3 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H), 2.43 (t, J=7.5 Hz, 2H), 1.64-1.42 (m, 4H), 0.94 (t, J=6.9 Hz, 3) ppm. 13C NMR (75 MHz, CDCl3) δ 146.4, 132.1, 131.1, 123.3, 96.6, 79.1, 30.3, 21.9, 19.1, 13.4 ppm. 1-(1-Heptynyl)-4-nitrobenzene (4d) was obtained as a brown oil (234.6 mg, 90%). 1H-NMR (300 MHz, CDCl3) δ ppm 8.13 (d, J=9.0 Hz, 2H), 7.49 (d, J=9.0 Hz, 2H), 2.41 (t, J=6.9 Hz, 2H), 1.65-1.55 (m, 2H), 1.46-1.28 (m, 4H), 0.90 (t, J=7.2 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ146.4, 132.1, 131.1, 123.3, 96.7, 79.1, 31.0, 27.9, 22.1, 19.4, 13.8. 1-(1-Decynyl)-4-nitrobenzene (4e) was obtained as a yellow oil (131 mg, 42%); 1H-NMR (300 MHz, CDCl3) δ 8.14 (d, J=8.7 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 2.42 (t, J=7.2 Hz, 2H), 1.63-1.58 (m, 2H), 1.43 (m, 2H), 1.28 (m, 8H), 0.87 (t, J=6.3 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ 146.4, 132.1, 131.1, 123.3, 96.7, 79.1, 31.7, 29.0, 28.9, 28.8, 28.2, 22.5, 19.4, 13.9 ppm. 1-(1-Dodecynyl)-4-nitrobenzene (4f). Obtained as a brown oil (216 mg, 63%); 1H-NMR (300 MHz, CDCl3) δ 8.14 (d, J=9.0 Hz, 2H), 7.50 (d, J=8.7 Hz, 2H), 2.42 (t, J=6.9 Hz, 2H), 1.63-1.55 (m, 2H), 1.45-1.40 (m, 2H), 1.25 (m, 12H), 0.86 (t, J=6.9 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ 146.4, 132.1, 131.1, 123.3, 96.7, 79.1, 31.8, 29.4, 29.2, 29.0, 28.8, 28.3, 22.5, 19.4, 14.0 ppm. 1-Nitro-4-(tetradec-1-yn-1-yl)benzene (4g) was obtained as a yellow solid (344 mg, 99%); 1H-NMR (300 MHz, CDCl3) δ 8.13 (d, J=9.0 Hz, 2H), 7.48 (d, J=9.0 Hz, 2H), 2.41 (t, J=6.9 Hz, 2H), 1.62-1.57 (m, 2H), 1.44-1.38 (m, 2H), 1.24 (m, 16H), 0.86 (t, J=6.9 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ 146.3, 132.0, 131.1, 123.3, 96.6, 79.1, 31.8, 29.5, 29.4, 29.3, 29.0, 28.8, 28.3, 22.6, 19.4, 13.9 ppm. 1-(4-Methylpent-1-ynyl)-4-nitrobenzene (4h) was obtained as a brown oil (187 mg, 77%); 1H-NMR (300 MHz, CDCl3) δ 8.14 (d, J=9.0 Hz, 2H), 7.50 (d, J=8.7 Hz, 2H), 2.33 (d, J=6.3 Hz, 2H), 1.96-1.87 (m, J=6.6 Hz, 1H), 1.04 (d, J=6.6 Hz, 6H) ppm. 13C NMR (75 MHz, CDCl3) δ 146.4, 132.1, 131.1, 123.3, 95.6, 80.1, 28.5, 27.9, 21.9 ppm. 1-(5-Methylhex-1-ynyl)-4-nitrobenzene (4i) was obtained as a light brown oil (232 mg, 87%); 1H-NMR (300 MHz, CDCl3) δ 8.15 (d, J=8.4 Hz, 2H), 7.51 (d, J=7.5 Hz, 2H), 2.44 (t, 2H), 1.76-1.70 (m, 1H), 1.55-1.48 (m, 2H), 0.95 (d, J=6.6 Hz, 6H) ppm. 13C NMR (75 MHz, CDCl3) δ 146.4, 132.1, 131.1, 123.3, 96.7, 79.1, 37.2, 27.2, 22.0, 17.5 ppm. 1-(3,3-Dimethylbut-1-ynyl)-4-nitrobenzene (4j) was obtained as a bright yellow solid (91.1 mg, 37%); 1H-NMR (300 MHz, CDCl3) δ 8.23 (d, J=7.8 Hz, 1H), 8.16 (d, J=7.5 Hz, 1H), 7.50-7.46 (dd, J=3.3, 7.8, 4.2 Hz, 2H), 1.34 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3) δ 142.7, 131.7, 125.5, 122.0, 100.9, 79.1, 30.8, 30.7, 28.0 ppm. 1-Nitro-4-(phenylethynyl)benzene (4k) was obtained as a bright yellow solid (239 mg, 89%); 1H-NMR (300 MHz, CDCl3) δ 8.20 (d, J=8.7 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 7.57-7.54 (dd, J=6.3, 1.8, 3.3 Hz, 2H), 7.40-7.37 (m, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ 146.8, 132.1, 131.7, 129.2, 128.5, 123.5, 122.0, 94.6, 87.5 ppm. 1-(Cyclohexylethynyl)-4-nitrobenzene (41) was obtained as a brown oil (284 mg, 99%); 1H-NMR (300 MHz, CDCl3) δ 8.11 (d, J=9.0 Hz, 2H), 7.48 (d, J=7.5 Hz, 2H), 2.63-2.54 (m, 1H), 1.87-1.82 (m, 2H), 1.75-1.67 (m, 2H), 1.55-1.46 (m, 2H), 1.39-1.22 (m, 4H) ppm. 13C NMR (75 MHz, CDCl3) δ 146.3, 132.1, 131.1, 123.3, 100.5, 79.1, 32.9, 29.6, 25.6, 24.7 ppm. General Procedure for Hydrogenation of 4a-m.