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Organic Letters

Volumn 11, Issue 8, 2009, Pages 1837-1840

TMPZnCI.LiCI: A new active selective base for the directed zincation of sensitive aromatics and heteroaromatics

(2) Mosrin, Marc a Knochel, Paul a

a UNIVERSITY OF MUNICH (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 65249111732 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol900342a Document Type: Article

Times cited : (173)

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- Typical Procedure, 2, 4-Difluoro-l-nitrobenzene 15 (159 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl-LiCl (2, 1.3 M in THF, 0.85 mL, LI mmol) at 25 °C, and the reaction mixture was then stirred at this temperature for 45 min. CuCN-2LiCl (1.0 M solution in THF, 1.1 mL, 1.1 mmol) was slowly added at -40 °C, and the reaction mixture was stirred at the same temperature for 30 min. Then, benzoyl chloride (281 mg, 2.0 mmol) was added dropwise at -40 °C, and the resulting mixture was allowed to warm up slowly to 25 °C overnight. The reaction mixture was then quenchend with a saturated aq NH 4C1 solution (20 mL, extracted with diethyl ether (3 × 50 mL, and dried over anhydrous Na2S04. After filtration, the solvent was evaporated in vacuo. Purification by flash chromatography (CH 2Cl2/pentane, 1:2) furnished compound 17b 221 m
- 2/pentane, 1:2) furnished compound 17b (221 mg, 84% yield) as a colorless solid.

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