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Synlett 2012; 23(15): 2247-2250
DOI: 10.1055/s-0031-1290451
DOI: 10.1055/s-0031-1290451
letter
Copper-Catalyzed Cyanation of Arylboronic Acids Using DDQ as Cyanide Source
Authors
Further Information
Publication History
Received: 18 May 2012
Accepted after revision: 23 June 2012
Publication Date:
08 August 2012 (online)
Abstract
In this paper, a copper-catalyzed cyanation of arylboronic acids is achieved with DDQ, providing nitriles with good yields. This new approach represents a safe method for the synthesis of aryl nitriles.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information (PDF)
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- 17 General Procedure of Cyanation Protocol of Arylboronic Acids with DDQ Under air, a reaction tube was charged with arylboronic acids (0.2 mmol), DDQ (45.2 mg, 0.2 mmol), Cu(OTf)2 (7.2 mg, 10 mol%), K2CO3 (41.4 mg, 0.3 mmol), Ag2CO3 (55 mg, 0.2 mmol), and dry DMF (2 mL). The mixture was stirred at 100 °C for 20 h. After the completion of the reaction, monitored by TLC, the solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to give the product. 4-(Methylthio)benzonitrile (3ac) Yellowlish solid; mp 61–62 °C. 1H NMR (300 MHz, CDCl3): δ = 7.53 (d, J = 8.7 Hz, 2 H), 7.26 (d, J = 8.7 Hz, 2 H), 2.51 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 146.1, 132.2, 125.6, 119.0, 107.7, 14.7. IR (neat): ν = 2223, 1699, 1593, 1483, 1434, 1361, 1218, 1089, 816 cm–1. HRMS (EI): m/z calcd for C8H7NS [M+]: 149.0299; found: 149.0291. Methyl 4-Cyanobenzoate (3al) Yellowlish solid; mp 67–68 °C. 1H NMR (300 MHz, CDCl3): δ = 8.12 (d, J = 8.1 Hz, 2 H), 7.73 (d, J = 8.1 Hz, 2 H), 3.95 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 165.4, 133.9, 132.2, 130.0, 117.9, 116.4, 52.6. IR (neat): ν = 2221, 1699, 1582, 1424, 1358, 1210, 1089 cm–1. HRMS (EI): m/z calcd for C9H7NO2 [M+]: 161.0477; found: 161.0486.