Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 12, Pages 5364-5370Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3008258
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Funding
- Indian Institute of Science
- CSIR
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An excellent utility of Schmidt reaction of aldehydes to access corresponding nitriles in an instantaneous reaction is demonstrated. The reaction of aldehydes with NaN3 and TfOH furnishes the corresponding nitriles in near quantitative yields and tolerates a variety of electron-withdrawing and electron-donating substituents on the substrates. Formanilides, a common side product in Schmidt reaction, is not observed in this reaction. Besides these advantages, the salient feature of this reaction is that it exhibits a remarkable chemoselectivity, as acid and ketone functionalities are well tolerated under the reaction conditions. The reaction is easily scalable, high yielding, and nearly instantaneous.
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