SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 12, 2007, Pages 1843-1850

Palladium-catalyzed copper-free sonogashira coupling reaction in water and acetone

(2) Shi, Shengyin a Zhang, Yuhong a

a ZHEJIANG UNIVERSITY (China)

Author keywords

Aqueous; Copper free; Palladium catalyzed; Sonogashira coupling

Indexed keywords

ACETONE; ALKYNE; AROMATIC COMPOUND; BROMIDE; COPPER; PALLADIUM; PHOSPHINE; PIPERIDINE; TRIPHENYLPHOSPHINE; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; SONOGASHIRA REACTION; SYNTHESIS; TERMINAL SEQUENCE;

EID: 34547617739 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984533 Document Type: Article

Times cited : (36)

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- General Procedure for the Sonogashira Reaction of Aryl Iodides A mixture of NaOH (0.08 g, 2 mmol, Pd(OAc)2 (2 mg, 1 mol, distilled H2O (3 g, and acetone (3 g, 3.8 mL) was stirred for 5 min. Then, aryl iodides (1 mmol) and terminal alkynes (1.2 mmol) were introduced and the mixture of the reaction was heated to 60°C for 1 h. Afterward, the reaction solution was cooled to r.t. and extracted four times with Et2O (4 x 10 mL, The combined organic phase was analyzed by GC and GC-MS. Further purification of the product was achieved by flash chromatography on a silica gel column. 1-(2-Phenylethynyl)naphthalene (Table 2, entry 6, 1H NMR (500 MHz, CDCl3, TMS, δ, 8.43-8.45 (d, 1 H, J, 8.35 Hz, 7.72-7.80 (m, 3 H, 7.61-7.63 (m, 2 H, 7.55 (m, 1 H, 7.46-7.48 (m, 1 H, 7.33-7.38 (m, 1 H, 7.30-7.32 (m, 3 H, MS (EI, m/z, 229 (20, M, 1, 228 (100, M, 226 43
- +], 226 (43).

69
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- General Procedure for the Sonogashira Reaction of Aryl Bromides and Polyhaloaryls A mixture of piperidine (0.17 g, 2 mmol; for dihalides, 4 mmol; for trihalides, 6 mmol; for tetrahalides, 8 mmol, PdCl2 (11 mg, 5 mol, for dihalides, PdCl2, 10 mol, for trihalides, PdCl 2, 15 mol, for tetrahalides, PdCl2, 20 mol, PPh 3 (26 mg, 10 mol, for dihalides, PPh3, 20 mol, for trihalides, PPh3, 30 mol, for tetrahalides, PPh3, 40 mol, distilled H2O (3 g, and acetone (3 g, 3.8 mL) was stirred for 5 min under nitrogen. Then, aryl bromides or polyhaloaryls (1 mmol) and terminal alkynes (1.2 mmol; for dihalides, alkynes, 2.4 mmol; for trihalides, alkynes, 3.6 mmol; for tetrahalides, alkynes, 4.8 mmol) were introduced and the mixture of the reaction was heated to 60°C for the indicated time under nitrogen. Afterwards, the reaction solution was cooled to r.t. and extracted wit
- +], 139 (10).

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