Direct Transformation of N,N-Dimethylformamide to −CN: Pd-Catalyzed Cyanation of Heteroarenes via C–H Functionalization

Direct Transformation of N,N-Dimethylformamide to −CN: Pd-Catalyzed Cyanation of Heteroarenes via C–H Functionalization

This paper describes the direct cyanation of indoles and benzofurans employing N,N-dimethylformamide (DMF) as both reagent and solvent. Isotopic labeling experiments indicated that both the N and the C of the cyano group derived from DMF. This transformation offers an alternative method for preparin...

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Veröffentlicht in:Journal of the American Chemical Society 2011-08, Vol.133 (32), p.12374-12377
Hauptverfasser: Ding, Shengtao, Jiao, Ning
Format: Artikel
Sprache:eng
Schlagworte:
Benzofurans - chemistry
Catalysis
Cyanides - chemistry
Dimethylformamide
Formamides - chemistry
Indoles - chemistry
Palladium - chemistry
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Zusammenfassung:This paper describes the direct cyanation of indoles and benzofurans employing N,N-dimethylformamide (DMF) as both reagent and solvent. Isotopic labeling experiments indicated that both the N and the C of the cyano group derived from DMF. This transformation offers an alternative method for preparing aryl nitriles, though it is currently limited in scope to indoles and benzofurans.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja204063z