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Literature DB >> 20359171

Oxidative amidation and azidation of aldehydes by NHC catalysis.

Abstract

N-heterocyclic carbene catalyzed oxidative amidations of various aldehydes to the corresponding hexafluoroisopropylesters by using the readily available organic oxidant A are described. The hexafluoroisopropylesters prepared in situ are shown to be highly useful active esters for amide bond formation. In addition, oxidative azidation of aldehydes is presented. These mild organocatalytic processes do not use any transition metal.

Entities: Chemical Disease

Mesh：

Substances：
Aldehydes
Amides
Azides

Year: 2010 PMID： 20359171 DOI： 10.1021/ol1004643

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

20 in total

Review 1. Rethinking amide bond synthesis.

Authors: Vijaya R Pattabiraman; Jeffrey W Bode
Journal: Nature Date: 2011-12-21 Impact factor: 49.962

2. Nickel-catalyzed dehydrogenative cross-coupling: direct transformation of aldehydes into esters and amides.

Authors: Aaron M Whittaker; Vy M Dong
Journal: Angew Chem Int Ed Engl Date: 2014-11-25 Impact factor: 15.336

3. α,β-Unsaturated acyl azoliums from N-heterocyclic carbene catalyzed reactions: observation and mechanistic investigation.

Authors: Jessada Mahatthananchai; Pinguan Zheng; Jeffrey W Bode
Journal: Angew Chem Int Ed Engl Date: 2011-01-05 Impact factor: 15.336

4. Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors: Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal: Adv Synth Catal Date: 2012-04-19 Impact factor: 5.837

Oxidative amidation and azidation of aldehydes by NHC catalysis.

Review 1. Rethinking amide bond synthesis.

2. Nickel-catalyzed dehydrogenative cross-coupling: direct transformation of aldehydes into esters and amides.

3. α,β-Unsaturated acyl azoliums from N-heterocyclic carbene catalyzed reactions: observation and mechanistic investigation.

4. Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Review 5. A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

6. The effect of the N-mesityl group in NHC-catalyzed reactions.

7. N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes.

Review 8. Recent advances in N-heterocyclic carbene-based radical catalysis.

9. NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes.

10. Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.