Efficient and Fast Method for the Preparation of Diaryl Ketones at Room Temperature

Abdol Reza Hajipour; Raheleh Pourkaveh

doi:10.1055/s-0033-1341070

Synlett, Table of Contents

Synlett 2014; 25(08): 1101-1105
DOI: 10.1055/s-0033-1341070

letter

Efficient and Fast Method for the Preparation of Diaryl Ketones at Room Temperature

Abdol Reza Hajipour*

^aDepartment of Pharmacology, University of Wisconsin Medical School, 1300 University Avenue, Madison, WI 53706-1532, USA

^bPharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran Fax: +98(311)3912350 Email: haji@cc.iut.ac.ir

,

Raheleh Pourkaveh

^bPharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran Fax: +98(311)3912350 Email: haji@cc.iut.ac.ir

› Author Affiliations

Abstract

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Abstract

Palladium-catalyzed cross-coupling reaction of arylboronic acids with acid chlorides at room temperature under phosphine-free conditions affords the corresponding aromatic ketones in excellent yields within short times. This synthetic method overcomes common disadvantages of Friedel–Crafts acylation procedures and is compatible with both electron-donating and electron-withdrawing substituents on the aryl ring of the acyl chlorides.

Key words

palladium - aromatic ketone - acid chloride - arylboronic acid - room temperature

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References

References and Notes
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41 Preparation of Catalyst; General Procedure: (–)-Nicotine (1 mmol, 0.16 mL) and benzyl chloride (4 mmol, 0.46 mL) were mixed under solvent-free conditions and the reaction mixture was heated at 70 °C for 6 h. The reaction mixture was treated with CH₂Cl₂ (5 × 6 mL) to remove the unreacted materials and the organic phase was separated. The residue (0.340 g, 82%) was mixed with PdCl₂ (0.177 g PdCl₂ per 0.415 g dibenzylated nicotinium salt) in acetone and heated at reflux for 12 h. The supernatant was decantated and washed with acetone (3 × 5 mL) to produce the catalyst (0.530 g, 91%) as a brown powder. Suzuki-Type Cross-Coupling Reaction; Typical Procedure: An oven-dried round-bottom flask was charged with phenylboronic acid (4 mmol, 0.487 g), benzoyl chloride (2 mmol, 0.23 mL), K₂CO₃ (4.5 mmol, 0.621 g), CHCl₃ (2 mL), and [DBNT][PdCl₄] (1 mol%, 0.023 g). The reaction mixture was stirred at r.t. for 35 min, then the solution was extracted with water and EtOAc and separated by column chromatography (silica gel; EtOAc–hexanes, 1:9). All products are known compounds and were characterized by comparing their FT-IR and ¹H NMR spectra with those reported in the literature (see Yu et al.⁹).

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