ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

Chemoselective Schmidt Reaction Mediated by Triflic Acid: Selective Synthesis of Nitriles from Aldehydes

Rokade, Balaji V and Prabhu, Kandikere Ramaiah (2012) Chemoselective Schmidt Reaction Mediated by Triflic Acid: Selective Synthesis of Nitriles from Aldehydes. In: JOURNAL OF ORGANIC CHEMISTRY, 77 (12). pp. 5364-5370.

[img] PDF
JOC_jou_org_che_77_12_5364-5370_2012.pdf - Published Version
Restricted to Registered users only

Download (325Kb) | Request a copy
[img] PDF
jo3008258_si_001.pdf - Supplemental Material
Restricted to Registered users only

Download (3260Kb) | Request a copy
Official URL: http://dx.doi.org/10.1021/jo3008258

Abstract

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.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to American Chemical Society
Keywords: TRIMETHYLSILYL AZIDE;ALKENYL NITRILES;EFFICIENT;ARYL; TRANSFORMATION;ALKALOIDS;CYANATION;OXIDATION;HALIDES;KETONES
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 14 Jul 2012 08:05
Last Modified: 14 Jul 2012 08:08
URI: http://eprints.iisc.ernet.in/id/eprint/44795

Actions (login required)

View Item View Item