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Synlett

Volumn , Issue 6, 2007, Pages 969-973

Palladium-catalyzed cross-coupling reaction of a sulfoximine with aryl dichlorides under microwave irradiation

(2) Harmata, Michael a Hong, Xuechuan a

a UNIVERSITY OF MISSOURI (United States)

Author keywords

Coupling reaction; Microwave irradiation; Palladium; Sulfoximine

Indexed keywords

1,4 DICHLOROBENZENE; FUNCTIONAL GROUP; PALLADIUM; SULFOXIMINE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; MICROWAVE IRRADIATION;

EID: 34247257267 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-973872 Document Type: Article

Times cited : (14)

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36
- 34247229853
- General Procedure for Coupling of Sulfoximines with Aryl Dichlorides, Procedure A To 5 mL of toluene in a 10 mL microwave tube was successively added aryl dichlorides (1.0 equiv, R)-sulfoximine (4.0 equiv, rac-BINAP (7.5 mol, Pd(OAc)2 (5 mol, and Cs 2CO3 (14 equiv) under N2 atmosphere. The reaction mixture was stirred at r.t. for 30 min, then irradiated under vigorous stirring for 1.5 h at 135°C (constant temperature) and 200 W (irradiation power, The reaction was cooled down and diluted with CH2Cl 2, filtered through a pad of Celite® and concentrated in vacuo. The residue was purified by flash chromatography. Procedure B To 5 mL of toluene in a 10 mL microwave tube was successively added aryl chloride (1.5 mmol, R)-sulfoximine (0.3 mmol, rac-BINAP (7.5 mol, Pd(OAc)2 (5 mol, and Cs2CO3 (0.42 mmol) under N2 atmosphe
- 2, filtered through a pad of Celite® and concentrated in vacuo. The residue was purified by flash chromatography (30-40% EtOAc-hexane).

37
- 34247268753
- Data for Selected Compounds Compound 3 (procedure A, colorless liquid, yield 42, IR: 3064, 3019, 2925, 1589, 1474, 1286, 1200, 1090 cm-1. 1H NMR (300 MHz, CDCl3, δ, 8.06-8.03 (m, 2 H, 7.60-7.53 (m, 3 H, 7.31 (dd, J, 7.9, 1.5 Hz, 1 H, 7.19 (dd, J, 7.9, 1.5 Hz, 1 H, 6.97 (td, J, 7.5, 1.5 Hz, 1 H, 6.82 (td, J, 7.5, 1.5 Hz, 1 H, 3.25 (s, 3 H, 13C NMR (75.5 MHz, CDCl3, δ, 142.1, 139.0, 133.4, 129.8, 129.5, 128.5, 127.1, 123.9, 122.7, 45.6. HRMS: m/z calcd for C13H 12ClNOSNa [M, Na, 288.0220; found 288.0228, α]D25 12.25 (c 2.4, CHCl3, Compound 5 (procedure B, colorless liquid, yield 92, IR: 3060, 3015, 2949, 2921, 1732, 1585, 1442, 1298, 1262, 1176, 1033 cm-1 1H NMR (500 MHz, CDCl3, δ, 7.98-7.96 (m, 2 H, 7.60-7.57 m, 1 H, 7.53
- 3).

38
- 34247269301
- 3).
- 3).

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