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Literature DB >> 23616241

Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

Ly Dieu Tran¹, James Roane, Olafs Daugulis.

Abstract

Amine meets arene: A method for direct amination of β-C(sp(2))-H bonds of benzoic acid derivatives and γ-C(sp(2))-H bonds of benzylamine derivatives has been developed. The reaction is catalyzed by Cu(OAc)2 and a Ag2CO3 cocatalyst, and shows high generality and functional-group tolerance, as well as providing a straightforward means for the preparation of ortho-aminobenzoic acid derivatives.

Entities: Chemical Gene

Year: 2013 PMID： 23616241 PMCID： PMC3734806 DOI： 10.1002/anie.201300135

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

51 in total

1. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

Review 2. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors: Dino Alberico; Mark E Scott; Mark Lautens
Journal: Chem Rev Date: 2007-01 Impact factor: 60.622

3. Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion.

Authors: Hung-Yat Thu; Wing-Yiu Yu; Chi-Ming Che
Journal: J Am Chem Soc Date: 2006-07-19 Impact factor: 15.419

4. Palladium-catalyzed C-H aminations of anilides with N-fluorobenzenesulfonimide.

Authors: Kai Sun; Yan Li; Tao Xiong; Jingping Zhang; Qian Zhang
Journal: J Am Chem Soc Date: 2011-01-20 Impact factor: 15.419

5. Palladium-catalyzed intermolecular directed C-H amidation of aromatic ketones.

Authors: Bin Xiao; Tian-Jun Gong; Jun Xu; Zhao-Jing Liu; Lei Liu
Journal: J Am Chem Soc Date: 2011-01-10 Impact factor: 15.419

6. Scope and mechanism of allylic C-H amination of terminal alkenes by the palladium/PhI(OPiv)2 catalyst system: insights into the effect of naphthoquinone.

Authors: Guoyin Yin; Yichen Wu; Guosheng Liu
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

7. Copper-catalyzed aerobic oxidative functionalization of an arene C-H bond: evidence for an aryl-copper(III) intermediate.

Authors: Amanda E King; Lauren M Huffman; Alicia Casitas; Miquel Costas; Xavi Ribas; Shannon S Stahl
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

1. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Review 2. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

3. Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion.

4. Palladium-catalyzed C-H aminations of anilides with N-fluorobenzenesulfonimide.

5. Palladium-catalyzed intermolecular directed C-H amidation of aromatic ketones.

6. Scope and mechanism of allylic C-H amination of terminal alkenes by the palladium/PhI(OPiv)2 catalyst system: insights into the effect of naphthoquinone.

7. Copper-catalyzed aerobic oxidative functionalization of an arene C-H bond: evidence for an aryl-copper(III) intermediate.

8. Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

9. Copper-promoted sulfenylation of sp2 C-H bonds.

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

1. Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

2. Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

3. Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.

4. Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

5. Bidentate, monoanionic auxiliary-directed functionalization of carbon-hydrogen bonds.

6. Cobalt-promoted dimerization of aminoquinoline benzamides.

7. Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

8. A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp(2) C-H Bond Amination.

9. Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

10. Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.