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Volumn , Issue 3, 2009, Pages 482-486

Highly regioselective heck coupling reactions of aryl halides and dihydropyran in the presence of an NHC-pyridine ligand

(3) Jarusiewicz, Jamiei a Kyung, Soo Yoo a Kyung, Woon Jung a

a UNIVERSITY OF SOUTHERN CALIFORNIA (United States)

Author keywords

Cyclic enol ether; Heck reaction; N heterocyclic carbine; Palladium; Pyridine ligand

Indexed keywords

EID: 62249127356 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087528 Document Type: Article

Times cited : (11)

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- General Procedure for the Synthesis of Palladium(II) Complex 5 To a solution of 4 (0.6 mmol) in anhyd CH2Cl2 (20 mL) was added Ag2O (0.3 mmol, and the reaction mixture was stirred at r.t. for 4 h. The reaction mixture was then gravity filtered and dried under nitrogen to obtain a silver complex as a white solid. The silver complex (0.4 mmol) was then suspended in a solution of MeCN (20 mL) in a foil-covered round-bottom flask. To the reaction mixture was then added Pd(OAc)2 (0.4 mmol, and the reaction mixture was stirred at r.t. for 24 h. The reaction mixture was then gravity filtered, and the filtrate was concentrated in vacuo to obtain 5 (100 mg, 38% over two steps) as an orange solid. 1H NMR (250 MHz, CDCl3, δ, 8.98-9.02 (m, 1 H, 7.82-7.90 (m, 1 H, 7.59 (d, J, 10.0 Hz, 1 H, 7.49-7.55 (m, 1 H, 7.32-7.45 (m, 4 H, 5.96 (br s, 2 H, 4.06 (s, 3 H, 2.02 s, 6 H, 13C N
- 3): δ = 178.1, 153.5, 153.4, 139.8, 134.5, 132.7, 125.0, 124.9, 124.4, 124.1, 110.9, 110.4, 51.40, 33.40, 22.60.

43
- 62249116088
- General Procedure for the Preparation of Substituted Dihydropyrans An oven-dried resealable Schlenk flask was evacuated and filled with argon, then were added 4-iodoanisole (117 mg, 0.5 mmol, 3,4-dihydro-2H-pyran (0.55 mL, 6 mmol, K2CO3 (104 mg, 0.75 mmol, DMF (1 mL, palladium complex 5 (22 mg, 0.05 mmol, The reaction mixture was stirred at 100°C. After 48 h the solution was then allowed to cool to r.t. EtOAc (20 mL) was added to the reaction mixture, and then the reaction mixture was washed with H2O (3 x 10 mL, The organic layer was dried over Na 2SO4. After filtration, solvent was evaporated and purified by column chromatography (hexanes-EtOAc, 19:1, to afford 2-(4-methoxy-phenyl)-3,4-dihydro-2H-pyran (76 mg, 80, as a light orange oil. Compound 11a: yellow oil (62 mg, 71, 1H NMR (250 MHz, CDCl3, δ, 7.43 (m, 1 H, 7.17-7.26 (m, 3 H, 6.56 d, J
- 11NO: C, 74.51; H, 6.88; N, 8.69. Found: C, 74.39; H, 6.91; N, 8.61.

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