Phenylacetylene → 1-phenethyl-5-phenyl-1H-1,2,3-triazole

HRID 387408Notes

Reaction equation

HRID 387408 reaction equation
[CH2:1]([N:9]=[N+:10]=[N-:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:12]1([C:18]#[CH:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C[C-]1C(C)=C(C)C(C)=C1C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru+].C1COCC1>[CH2:1]([N:9]1[C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:19][N:11]=[N:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 145976Benzene, (2-azidoethyl)-

Product 1

HCID 684319401-phenethyl-5-phenyl-1H-1,2,3-triazoleYield 89%

Reagents, catalysts & solvents 2

HCID 71310463Chlororuthenium(1+) 1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-ide--triphenylphosphane (1/1/2)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Phenethyl azide (148 mg, 1 mmol), phenylacetylene (113 mg, 1.1 mmol), Cp*RuCl(PPh3)2 (8 mg, 0.01 mmol, 1 mol %). Solvent: THF, 10 mL, 60° C., 2 hours. Off-white product obtained in 89% yield (221 mg). ESI-MS: m/z 250, [M+H].

Workup

  1. customOff-white product obtained in 89% yield (221 mg)

Sources & evidence

ORD record
ord-4904ba8c1f55414f801ba6c95f0974fa
Source dataset
uspto-grants-2013_02
Patent number
US08372986B2

Reaction notes

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