Acetonitrile derivatives as carbonyl synthons. One-pot preparation of diheteroaryl ketones via a strategy of sequential SNAr substitution and oxidation |
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| Authors: | Yin Zhiwei Zhang Zhongxing Kadow John F Meanwell Nicholas A Wang Tao |
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| Institution: | Department of Chemistry, The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA. |
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| Abstract: | The anion of 2-aryl acetonitrile derivatives reacted with a variety of heteroaryl chlorides or bromides in an S(N)Ar manifold to afford intermediate anions which were susceptible to oxidation. The addition of sodium peroxide and aqueous NH(4)OAc solution effected oxidation to afford aryl heteroaryl ketones in good yields. Aryl acetonitrile derivatives are thus umpolung-type synthons of the corresponding aryl carbonyl functionality. |
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