Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 4, Pages 1437-1441Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob02321a
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- University of Torino
- Ministero dell'Universita e della Ricerca
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Arene and heteroarenediazonium o-benzenedisulfonimides can be used as efficient reagents in Sand-meyer cyanation. This work reports such reactions carried out by us under very mild conditions using tetrabutyl ammonium cyanide as a safe cyanide source and, interestingly, without the need for a Cu catalyst. The reactions have given rise to aryl nitriles in good yields ( 25 examples, average yield 75%). A good amount of o-benzenedisulfonimide was recovered from each reaction and then reused to prepare other salts. Mechanistic insights have allowed us to highlight the fundamental role of the o-benzenedisulfonimide anion as an electron transfer agent.
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