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Synlett 2015; 26(07): 950-952
DOI: 10.1055/s-0034-1380150
DOI: 10.1055/s-0034-1380150
letter
Facile Synthesis of Cyanoarenes from Quinones by Reductive Aromatization of Cyanohydrin Intermediates
Further Information
Publication History
Received: 18 December 2014
Accepted after revision: 14 January 2015
Publication Date:
19 February 2015 (online)
Abstract
A novel synthesis of cyanoarenes from quinones by using PCl3 as the reagent for reductive aromatization of cyanohydrin intermediates is reported. In situ IR spectroscopic measurements were conducted to monitor the reactions and to develop a convenient one-pot protocol. 1,4-Dicyanobenzene and 9,10-dicyanoanthracene were prepared by the new procedure.
Supporting Information
- including complete experimental and instrumental details for the synthesis and characterization is available online at http://dx.doi.org/10.1055/s-0034-1380150.
- Supporting Information
-
References and Notes
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- 12 General Procedure (One-Pot): 1,4-Benzoquinone (1.0 equiv) was dissolved in MeCN (1 M) and added to a suspension of CsF (0.2 equiv) in MeCN (0.2 M) at 0 °C. The reaction was carefully purged with argon and TMSCN (2.0 equiv) was added dropwise, followed by another two additions after 4 min (0.1 equiv) and 6 min (0.1 equiv). After 10 min of total stirring time, DMF (2 small drops) and PCl3 (1.0 equiv) were added. The reaction was allowed to warm to r.t. and stirred for 90 min. The resulting suspension was diluted with CH2Cl2 and filtered through a pad of silica using CH2Cl2 as the eluent. Evaporation of the solvent afforded 1,4-dicyanobenzene (2) as a white solid (30% yield).