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Literature DB >> 18557628

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

Zhihui Zhang¹, Ying Yu, Lanny S Liebeskind.

Abstract

A general nonoxidative N-amidation of organostannanes and boronic acids has been developed. Under nonbasic conditions a wide variety of aryl, alkenyl, and heteroaryl organostannanes and boronic acids couple efficiently with O-acetyl hydroxamic acids in the presence of Cu(I) sources.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18557628 PMCID： PMC2664512 DOI： 10.1021/ol8009682

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

17 in total

1. The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperature: synthesis of aryloxyamines.

Authors: H M Petrassi; K B Sharpless; J W Kelly
Journal: Org Lett Date: 2001-01-11 Impact factor: 6.005

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

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

3. 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

4. Catalytic activities of Cu(II) complexes with nitrogen-chelating bidentate ligands in the coupling of imidazoles with arylboronic acids.

Authors: J P Collman; M Zhong; C Zhang; S Costanzo
Journal: J Org Chem Date: 2001-11-16 Impact factor: 4.354

5. 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

6. Enamide synthesis by copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts.

Authors: Yuri Bolshan; Robert A Batey
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

7. Ligand- and base-free copper(II)-catalyzed C-N bond formation: cross-coupling reactions of organoboron compounds with aliphatic amines and anilines.

Authors: Tan D Quach; Robert A Batey
Journal: Org Lett Date: 2003-11-13 Impact factor: 6.005

8. 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

9. A simple, modular synthesis of substituted pyridines.

Authors: Songbai Liu; Lanny S Liebeskind
Journal: J Am Chem Soc Date: 2008-05-09 Impact factor: 15.419

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

Authors: Songbai Liu; Ying Yu; Lanny S Liebeskind
Journal: Org Lett Date: 2007-04-20 Impact factor: 6.005

9 in total

1. Non-Deprotonative Primary and Secondary Amination of (Hetero)Arylmetals.

Authors: Zhe Zhou; Zhiwei Ma; Nicole Erin Behnke; Hongyin Gao; László Kürti
Journal: J Am Chem Soc Date: 2016-12-23 Impact factor: 15.419

Review 2. Cross-Coupling of Heteroatomic Electrophiles.

Authors: Katerina M Korch; Donald A Watson
Journal: Chem Rev Date: 2019-06-11 Impact factor: 60.622

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

Authors: Minh H Nguyen; Amos B Smith
Journal: Org Lett Date: 2013-09-03 Impact factor: 6.005

4. Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

Authors: David W Lin; Takeshi Masuda; Moritz B Biskup; Jonathan D Nelson; Phil S Baran
Journal: J Org Chem Date: 2011-01-20 Impact factor: 4.354

5. Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors: Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal: J Am Chem Soc Date: 2016-10-18 Impact factor: 15.419

6. Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor.

Authors: Cheng Zhang; C James Chou
Journal: Org Lett Date: 2016-10-19 Impact factor: 6.005