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Literature DB >> 12203909

Synthesis of aza-heterocycles from oximes by amino-Heck reaction.

Abstract

Oxidative addition of oximes to palladium(0) complexes generates alkylideneaminopalladium(II) species, which are utilized as key intermediates for carbon-nitrogen bond formation. Various aza-heterocycles, such as pyrrole, pyridine, isoquinoline, spiroimine, and azaazulene, can be synthesized from O-pentafluorobenzoyloximes having an olefinic moiety via an intramolecular Heck-type reaction (amino-Heck reaction) by treatment with a catalytic amount of a Pd(0) complex. Copyright 2002 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.

Entities: Chemical

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Year: 2002 PMID： 12203909 DOI： 10.1002/tcr.10030

Source DB: PubMed Journal: Chem Rec ISSN： 1528-0691 Impact factor: 6.771

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Cited

16 in total

1. Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

Authors: Todd K Hyster; Tomislav Rovis
Journal: Chem Commun (Camb) Date: 2011-10-10 Impact factor: 6.222

9. Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes.

Authors: Nicholas L Reed; Grace A Lutovsky; Tehshik P Yoon
Journal: J Am Chem Soc Date: 2021-04-15 Impact factor: 15.419

10. The oxime portmanteau motif: released heteroradicals undergo incisive EPR interrogation and deliver diverse heterocycles.

Authors: John C Walton
Journal: Acc Chem Res Date: 2014-03-21 Impact factor: 22.384

Synthesis of aza-heterocycles from oximes by amino-Heck reaction.

1. Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

Review 2. Cross-Coupling of Heteroatomic Electrophiles.

3. Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations.

4. Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

5. Pd-catalyzed Semmler-Wolff reactions for the conversion of substituted cyclohexenone oximes to primary anilines.

6. N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes.

7. Heck-like Reactions Involving Heteroatomic Electrophiles.

8. N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

9. Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes.

10. The oxime portmanteau motif: released heteroradicals undergo incisive EPR interrogation and deliver diverse heterocycles.