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Literature DB >> 24415804

Vanadium-catalyzed oxidative Strecker reaction: α-C-H cyanation of para-methoxyphenyl (PMP)-protected primary amines.

Abstract

We describe an oxidative Strecker reaction that allows for direct cyanation of para-methoxyphenyl (PMP)-protected primary amines. A vanadium(V) complex was used as the catalyst and TBHP as the oxidant. The cyanation occurs at the α-C position bearing either an alkyl or an aromatic group. This method provides a direct access to α-aminonitrile from amines with one-carbon extension.

Entities: Chemical

Keywords: C–H cyanation; Oxidative Strecker reaction; Primary amine; Schiff base ligand; Vanadium catalyst

Year: 2014 PMID： 24415804 PMCID： PMC3885172 DOI： 10.1016/j.tetlet.2013.11.012

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

29 in total

1. Vanadium in Modern Organic Synthesis.

Authors: Toshikazu Hirao
Journal: Chem Rev Date: 1997-12-18 Impact factor: 60.622

2. Vanadium catalysis of the oxidation of catechol amines, dihydroxyphenylalanine and 5-hydroxyindoles.

Authors: G M MARTIN; E P BENDITT; N ERIKSEN
Journal: Nature Date: 1960-06-11 Impact factor: 49.962

3. New reactions of IBX: oxidation of nitrogen- and sulfur-containing substrates to afford useful synthetic intermediates.

Authors: K C Nicolaou; Casey J N Mathison; Tamsyn Montagnon
Journal: Angew Chem Int Ed Engl Date: 2003-09-05 Impact factor: 15.336

Vanadium-catalyzed oxidative Strecker reaction: α-C-H cyanation of para-methoxyphenyl (PMP)-protected primary amines.

1. Vanadium in Modern Organic Synthesis.

2. Vanadium catalysis of the oxidation of catechol amines, dihydroxyphenylalanine and 5-hydroxyindoles.

3. New reactions of IBX: oxidation of nitrogen- and sulfur-containing substrates to afford useful synthetic intermediates.

4. Enantioselective biocatalytic oxidative desymmetrization of substituted pyrrolidines.

5. Asymmetric strecker reactions.

6. Copper-catalyzed C-H oxidation/cross-coupling of α-amino carbonyl compounds.

7. A Highly Selective Vanadium Catalyst for Benzylic C-H Oxidation.

8. Efficient ruthenium-catalyzed aerobic oxidation of amines by using a biomimetic coupled catalytic system.

9. Convenient and clean synthesis of imines from primary benzylamines.

10. Oxidation of secondary amines catalyzed by dirhodium caprolactamate.

1. A simple method for the electrophilic cyanation of secondary amines.