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Volumn , Issue 7, 2007, Pages 1163-1165

Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes

(6) Shimizu, Masaki a Higashi, Masahiro a Takeda, Youhei a Jiang, Guofang a Murai, Masahito a Hiyama, Tamejiro a

a KYOTO UNIVERSITY (Japan)

Author keywords

Alkynes; Allenes; Fluorine; Lithium; Palladium

Indexed keywords

1,1 DICHLORO 3,3,3 TRIFLUOROACETONE; 3,3,3 TRIFLUOROPROPYNYLLITHIUM; ACETONE; ALLENE DERIVATIVE; BUTYLLITHIUM; CARBONYL DERIVATIVE; LITHIUM DERIVATIVE; PALLADIUM; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 34248191701 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-977422 Document Type: Article

Times cited : (20)

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37
- 34248232874
- Representative Procedure for Preparation of Compounds 5 To a solution of 4b (1.5 g, 6.6 mmol, p-toluenesulfonyl chloride (1.4 g, 7.2 mmol, 4-dimethylaminopyridine (40 mg, 0.33 mmol) in CH 2Cl2 (26 mL) was added Et3N (1.1 mL, 7.9 mmol) at 0°C. The resulting solution was stirred at r.t. for 2 h before quenching with sat. aq NH4Cl solution (20 mL) at 0°C. The aqueous layer was extracted with CH2Cl2 (3 x 20 mL) and the combined organic solvent was washed with sat. aq NaCl solution (60 mL, dried over anhyd MgSO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (hexane-EtOAc, 15:1) to give 5b (2.4 g, 95% yield) as a colorless solid. Mp 48°C. Rf, 0.45 (hexane-EtOAc, 4:1, 1H NMR (400 MHz, CDCl3, δ, 2.13-2.28 (m, 2 H, 2.46 (s, 3 H, 2.74-2.82 (m, 2 H, 5.07-5.11 (m, 1 H, 7.15 d
- +]: 382.0851; found: 382.0839.

38
- 34248219405
- Representative Procedure for the Preparation of Compounds 6 To a solution of 5b (0.10 g, 0.26 mmol) and Pd(PPh3)4 (15 mg, 0.013 mmol) in THF (2.6 mL) was added PhZnCl (0.79 mL, 0.79 mmol, 1.0 M in THF) at 0°C. The solution was stirred at r.t for 2 h before quenching with sat. aq NH4Cl solution (2 mL) at 0°C. The aqueous layer was extracted with EtOAc (3 x 2 mL, The combined organic solvent was washed with sat. aq NaCl solution (6 mL, dried over anhyd MgSO4, and concentrated by rotary evaporator. The crude product was purified by column chromatography on silica gel (hexane-EtOAc, 20:1) gave 6b (52 mg, 69% yield) as colorless solid; mp 29°C; Rf, 0.67 (hexane-EtOAc, 4:1, 1H NMR (400 MHz, CDCl3, δ, 2.54-2.67 (m, 2 H, 2.80-2.91 (m, 2 H, 5.96-6.01 (m, 1 H, 7.21-7.34 (m, 10 H, 13C NMR (101 MHz, CDCl3, δ, 29.9, 34.9, 99.2, 102.1 q
- +]: 288.1126; found: 288.1128.

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