Cobalt-catalyzed alkyne-dihalomethane-amine coupling: An efficient route for propargylamines

Tetrahedron Letters

Volumn 53, Issue 46, 2012, Pages 6199-6201

  Tang, Yanchi ^a   Xiao, Tiebo ^a   Zhou, Lei ^a,b  

^a SUN YAT SEN UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

Alkynes; Amines; Cobalt; Dihalomethane; Propargylamines

Indexed keywords

ALKANE DERIVATIVE; ALKYNE; AMINE; CARBON; COBALT; COBALT BROMIDE; COBALT COMPLEX; DIHALOMETHANE; FUNCTIONAL GROUP; HALOGEN; HYDROGEN; LIGAND; ORGANONITROGEN DERIVATIVE; PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SYNTHESIS;

EID: 85027918369     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.136     Document Type: Article

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49. Representative experimental procedure for cobalt-catalyzed three-component coupling of alkynes, dihaloalkanes, and amines. Synthesis of 4a: CoBr2 (10.9 mg, 10 mol %) and DBU (152 mg, 1 mmol) were suspended in CH3CN (2 mL) in a 5 mL schlenk tube under nitrogen. And then phenylacetylene (51 mg, 0.5 mmol), dichloromethane (126 mg, 1.5 mmol), and diethylamine (109.5 mg, 1.5 mmol) were added via syringe. The resulting solution was stirred at 80 -C for 24 h. After cooling to room temperature, the resulting mixture was filtered through a short path of silica gel, eluting with dichloromethane. The volatile compounds were removed in vacuo and the residue was purified by column chromatography (SiO2, hexane/ethyl acetate = 10:1) to give 4a as a colourless oil (79.5 mg, 85%).1H NMR (300 MHz, CDCl3) d 7.437.40 (m, 2H), 7.307.25 (m, 3H), 3.68 (s, 2H), 2.68 (q, J = 7.2 Hz, 4H), 1.16 (t, J = 7.2 Hz, 6H); 13C NMR (75 MHz, CDCl3): d = 131.8, 128.3, 128.0, 123.5, 85.3, 84.5, 47.6, 41.8, 12.9 ppm.