SCOPUS 정보 검색 플랫폼

Volumn , Issue 6, 2008, Pages 886-888

Copper-catalyzed, palladium-free carbonylative Sonogashira coupling reaction of aliphatic and aromatic alkynes with iodoaryls

(4) Tambade, Pawan J a Patil, Yogesh P a Nandurkar, Nitin S a Bhanage, Bhalchandra M a

a UNIVERSITY OF MUMBAI (India)

Author keywords

Alkynes; Carbonylation; Copper; Iodoaryls; Sonogashira

Indexed keywords

ALIPHATIC COMPOUND; ALKYNE DERIVATIVE; AROMATIC COMPOUND; COPPER DERIVATIVE; IODINE DERIVATIVE; PALLADIUM; PHOSPHINE; SOLVENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBONYLATION; CATALYSIS; CATALYST; PROTON NUCLEAR MAGNETIC RESONANCE; SONOGASHIRA REACTION;

EID: 42049116321 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042897 Document Type: Article

Times cited : (63)

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- 2O (10 mmol) in MeOH (20 mL) was added over a period of 30 min. The reaction mixture was stirred for 6 h and the resulting precipitate was filtered and dried. Yield 93%, mp 196-198°C.
- 2O (10 mmol) in MeOH (20 mL) was added over a period of 30 min. The reaction mixture was stirred for 6 h and the resulting precipitate was filtered and dried. Yield 93%, mp 196-198°C.

34
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- General Procedure To an 100 mL autoclave, phenylacetylene (3.0 mmol, iodobenzene (2.0 mmol, Cu(TMHD)2 (0.1 mmol, toluene (10 mL) and Et3N (6.0 mmol) were added. The mixture was first stirred for 10 min, then the vessel pressures 8-20 atm of CO and the reaction mixture was heated at 90°C for 14 h. After the reaction was complete, the mixture was extracted with EtOAc (3 x 10 mL, the combined organic extracts were dried over Na2SO4, and the solvent was removed under vacuum. The residue obtained was purified by column chromatography (silica gel, 60-120 mesh) using PE (60:80)-EtOAc as eluent to afford the pure products. All the compounds are known and were characterized by GC-MS (Shimadzu) and NMR (Varian 300 MHz, Spectroscopic Data of Representative Compounds Table 2, Entry 1: GC-MS: m/z, 206 [M, 178, 129 (100, 1H NMR (300 MHz, CDCl3, 25°C, δ, 749-7.54 m, 5 H, 7
- 3, 25°C): δ = 13.7, 19.1, 22.7, 29.9, 80.0, 97.0, 128.6, 129.7, 131.8, 134.0, 178.1 ppm.

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