Synlett 2018; 29(05): 593-596
DOI: 10.1055/s-0036-1589137
letter
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Addition of Arylboronic Acids to Alkyl Nitriles for Synthesis of Aryl Ketones in Fluorinated Solvent

Dong-Huai Tu
a  State Key Laboratory of Fluorine and Nitrogen Chemicals, Xi’an 710065, P. R. of China
b  Xi’an Modern Chemistry Research Institute, Xi’an 710065, P. R. of China   Email: lujian204@263.net
,
Yang Li
a  State Key Laboratory of Fluorine and Nitrogen Chemicals, Xi’an 710065, P. R. of China
b  Xi’an Modern Chemistry Research Institute, Xi’an 710065, P. R. of China   Email: lujian204@263.net
,
Bo Zhao
a  State Key Laboratory of Fluorine and Nitrogen Chemicals, Xi’an 710065, P. R. of China
b  Xi’an Modern Chemistry Research Institute, Xi’an 710065, P. R. of China   Email: lujian204@263.net
,
Yu-Jie Gu
a  State Key Laboratory of Fluorine and Nitrogen Chemicals, Xi’an 710065, P. R. of China
b  Xi’an Modern Chemistry Research Institute, Xi’an 710065, P. R. of China   Email: lujian204@263.net
,
Bo Wang
a  State Key Laboratory of Fluorine and Nitrogen Chemicals, Xi’an 710065, P. R. of China
b  Xi’an Modern Chemistry Research Institute, Xi’an 710065, P. R. of China   Email: lujian204@263.net
,
Ju-You Lu
a  State Key Laboratory of Fluorine and Nitrogen Chemicals, Xi’an 710065, P. R. of China
b  Xi’an Modern Chemistry Research Institute, Xi’an 710065, P. R. of China   Email: lujian204@263.net
,
Jian Lu*
a  State Key Laboratory of Fluorine and Nitrogen Chemicals, Xi’an 710065, P. R. of China
b  Xi’an Modern Chemistry Research Institute, Xi’an 710065, P. R. of China   Email: lujian204@263.net
› Author Affiliations
The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (21327011, 21503610), and the China Post-Doctoral Science Foundation (2016M592850).
Further Information

Publication History

Received: 01 September 2017

Accepted after revision: 29 October 2017

Publication Date:
28 November 2017 (eFirst)

Abstract

A mild and efficient nickel-catalyzed addition of arylboronic acids to alkyl nitriles in a fluorinated solvent for the synthesis of various aryl ketones is described. A broad range of arylboronic acids and alkyl nitriles were investigated, and the desired products were obtained with good to excellent yields under the optimized conditions. This method provides an opportunity for the synthesis of aryl ketones from alkyl nitriles, especially acetonitrile, with a non-noble metal catalyst in one pot.

Supporting Information

 
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  • 15 1-[4-(Trifluoromethyl)phenyl]ethanone (3i); Typical Procedure The reaction was carried out in an autoclave containing a 10 mL Teflon reaction tube. The tube was charged with arylboronic acid 1i (1.0 mmol, 189.9 mg), MeCN (2; 1.0 mL), NaHCO3 (2.0 equiv, 168.0 mg), H2O (2.0 mmol, 36.0 mg), and a magnetic stirrer bar. NiBr2·diglyme (17.6 mg, 5 mol%) and 1,10-phen (18.0 mg, 10 mol%) were then added to the tube, the autoclave was capped with a stopper and cooled with liquid N2, and HCFC-244bb (2.0 mL, 2.6 g) was added by self-suction. The mixture was stirred at 100 °C for 5 h, then cooled to r.t. Excess HCFC-244bb was carefully vented, and H2O (30 mL) was added to the mixture. The mixture was extracted with CH2Cl2 (3 × 15 mL), and the organic layers were combined, washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The crude product was purified by column chromatography [silica gel, hexane–EtOAc (20:1)] to give a colorless oil; yield: 142.9 mg (76%). 1H NMR (500 MHz, CDCl3): δ = 8.09 (d, J = 8.0 Hz, 2 H), 7.76 (d, J = 8.5 Hz, 2 H), 2.68 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 197.1, 139.8, 134.5 (q, JCF = 32.5 Hz), 128.7, 125.8 (q, JCF = 3.8 Hz), 123.7 (q, JCF = 271.1 Hz), 26.9. 19F NMR (470 MHz, CDCl3): δ = –63.1 (s, 3 F).
  • 16 1-(4-Hydroxyphenyl)heptan-1-one (3i) The reaction was carried as describe above with (4-hydroxyphenyl)boronic acid (1y; 1.0 mmol, 137.9 mg) and heptanenitrile (1.0 mL) to give a white solid; yield: 129.9 mg (63%); mp 62–63 °C. 1H NMR (500 MHz, CDCl3): δ = 7.91 (d, J = 8.5 Hz, 2 H), 6.91 (d, J = 9.0 Hz, 2 H), 6.67 (s, 1 H), 2.92 (t, J = 8.0 Hz, 2 H), 1.75–1.69 (m, 2 H), 1.40–1.35 (m, 2 H), 1.32–1.30 (m, 4 H), 0.88 (t, J = 7.0 Hz, 3 H). 13C NMR (125 MHz, CDCl3): δ = 200.3, 160.5, 130.8, 129.9, 115.4, 38.4, 31.7, 29.1, 24.8, 22.5, 14.0.