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Literature DB >> 17444649

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

Songbai Liu¹, Ying Yu, Lanny S Liebeskind.

Abstract

Catalytic quantities of copper(I) or copper(II) sources catalyze the N-imination of boronic acids and organostannanes through reaction with oxime O-carboxylates under nonbasic conditions. This method tolerates various functional groups and takes place efficiently using aryl, heteroaryl, and alkenyl boronic acids and stannanes.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17444649 PMCID： PMC2652698 DOI： 10.1021/ol070561w

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

13 in total

1. Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.

Authors: Hui Zhang; Qian Cai; Dawei Ma
Journal: J Org Chem Date: 2005-06-24 Impact factor: 4.354

2. Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols.

Authors: P S Herradura; K A Pendola; R K Guy
Journal: Org Lett Date: 2000-07-13 Impact factor: 6.005

3. An efficient diamine.copper complex-catalyzed coupling of arylboronic acids with imidazoles

Authors:
Journal: Org Lett Date: 2000-05-04 Impact factor: 6.005

4. Copper-catalyzed electrophilic amination of organozinc nucleophiles: documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons.

Authors: Ashley M Berman; Jeffrey S Johnson
Journal: J Org Chem Date: 2006-01-06 Impact factor: 4.354

5. Copper(I) catalysed cyclisation of unsaturated N-benzoyloxyamines: an aminohydroxylation via radicals.

Authors: Michael Noack; Richard Göttlich
Journal: Chem Commun (Camb) Date: 2002-03-07 Impact factor: 6.222

6. Cu(I)-mediated reductive amination of boronic acids with nitroso aromatics.

Authors: Ying Yu; Jiri Srogl; Lanny S Liebeskind
Journal: Org Lett Date: 2004-07-22 Impact factor: 6.005

7. A mild, nonbasic synthesis of thioethers. The copper-catalyzed coupling of boronic acids with N-thio(alkyl, aryl, heteroaryl)imides.

Authors: Cecile Savarin; Jiri Srogl; Lanny S Liebeskind
Journal: Org Lett Date: 2002-11-28 Impact factor: 6.005

8. A new catalytic hetero-Heck type reaction.

Authors: Juho Helaja; Richard Göttlich
Journal: Chem Commun (Camb) Date: 2002-04-07 Impact factor: 6.222

9. Copper-catalyzed electrophilic amination of diorganozinc reagents.

Authors: Ashley M Berman; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2004-05-12 Impact factor: 15.419

10. Synthesis of primary amines by the electrophilic amination of Grignard reagents with 1,3-dioxolan-2-one O-sulfonyloxime.

Authors: Mitsuru Kitamura; Takahiro Suga; Shunsuke Chiba; Koichi Narasaka
Journal: Org Lett Date: 2004-11-25 Impact factor: 6.005

11 in total

1. A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

Authors: Saki Ichikawa; Shaolin Zhu; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2018-06-12 Impact factor: 15.336

2. Mobilizing Cu(I) for carbon-carbon bond forming catalysis in the presence of thiolate. Chemical mimicking of metallothioneins.

Authors: Zhihui Zhang; Matthew G Lindale; Lanny S Liebeskind
Journal: J Am Chem Soc Date: 2011-03-30 Impact factor: 15.419

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

1. Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.

2. Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols.

3. An efficient diamine.copper complex-catalyzed coupling of arylboronic acids with imidazoles

4. Copper-catalyzed electrophilic amination of organozinc nucleophiles: documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons.

5. Copper(I) catalysed cyclisation of unsaturated N-benzoyloxyamines: an aminohydroxylation via radicals.

6. Cu(I)-mediated reductive amination of boronic acids with nitroso aromatics.

7. A mild, nonbasic synthesis of thioethers. The copper-catalyzed coupling of boronic acids with N-thio(alkyl, aryl, heteroaryl)imides.

8. A new catalytic hetero-Heck type reaction.

9. Copper-catalyzed electrophilic amination of diorganozinc reagents.

10. Synthesis of primary amines by the electrophilic amination of Grignard reagents with 1,3-dioxolan-2-one O-sulfonyloxime.

1. A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

2. Mobilizing Cu(I) for carbon-carbon bond forming catalysis in the presence of thiolate. Chemical mimicking of metallothioneins.

Review 3. Cross-Coupling of Heteroatomic Electrophiles.

4. Copper-catalyzed electrophilic amination of organolithiums mediated by recoverable siloxane transfer agents.

5. 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

6. A simple, modular synthesis of substituted pyridines.

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

8. Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation.

9. Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles.

10. Controlled Synthesis of Up-Conversion NaYF₄:Yb,Tm Nanoparticles for Drug Release under Near IR-Light Therapy.