Samarium Diiodide Induced Reductive Coupling of Nitriles with Azides

Su, Weike; Li, Yongshu; Zhang, Yongmin

doi:10.3184/030823401103168190

Cited by 6 publications

(6 citation statements)

References 23 publications

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“…We speculate that 25 may reduce azide 26 through a one-electron transfer to generate azide radical anion 27 . Following nitrogen gas extrusion and protonation, the resulting aminyl radical 28 may undergo a radical addition to the nitrile 34,35…”

Section: Resultsmentioning

confidence: 99%

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A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system

et al. 2011

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Using a system that accelerates the serendipitous discovery of new reactions by evaluating hundreds of DNA-encoded substrate combinations in a single experiment, we explored a broad range of reaction conditions for new bond-forming reactions. We discovered reactivity that led to a biomolecule-compatible, Ru(II)-catalyzed, visible light-induced azide reduction reaction. In contrast with current azide reduction methods, this reaction is highly chemoselective and is compatible with alcohols, phenols, acids, alkenes, alkynes, aldehydes, alkyl halides, alkyl mesylates, and disulfides. The remarkable functional group compatibility and mild conditions of this reaction enabled azide reduction to be performed on nucleic acid and oligosaccharide substrates without the detectable occurrence of side reactions. The reaction was also performed in the presence of a protein enzyme without loss of enzymatic activity, in contrast with two commonly used azide reduction methods. The visible light dependence of this reaction provides a means of photouncaging functional groups such as amines and carboxylates on biological macromolecules without using UV irradiation.

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Section: Resultsmentioning

confidence: 99%

“…Following nitrogen gas extrusion and protonation, the resulting aminyl radical 28 may undergo a radical addition to the nitrile. 34 , 35 …”

Section: Resultsmentioning

confidence: 99%

A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system

et al. 2011

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“…Melting points were uncorrected. 1 H NMR and 13 C NMR spectra were determined on a Bruker AC-400 instrument with DMSO-d 6 used as the solvent. Chemical shifts are expressed in ppm downfield from internal tetramethylsilane.…”

Section: Methodsmentioning

confidence: 99%

“…We have previously reported reductive coupling of azide compounds with nitriles. 13 Herein we wish to report a facile synthesis of 2,3-dihydro-2-aryl-4(1H)-quinazolinones in one pot via reductive cyclization of oazidobenzamides with aldehydes and ketones promoted by SmI 2 under mild and neutral conditions (Scheme 1).…”

mentioning

confidence: 99%

“…Although the detailed mechanism of the above reaction has not been clarified, the formation of products 3 may be described by the possible mechanism presented in Scheme 2. 13,17 In summary, the intermolecular reductive cyclisation reaction of azide compounds with aldehydes and ketones was studied and a facile synthesis of 2,3-dihydro-2-aryl-4(1H)quinazolinones was provided.…”

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confidence: 99%

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