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Literature DB >> 27654642

Copper-Catalyzed Amidation of Primary and Secondary Alkyl Boronic Esters.

Luis M Mori-Quiroz¹, Kirk W Shimkin¹, Sina Rezazadeh¹, Ryan A Kozlowski¹, Donald A Watson².

Abstract

The oxidative copper-catalyzed cross-coupling of functionalized alkyl boronic esters with primary amides is reported. Through the identification of appropriate diketimine ligands, conditions for efficient coupling of both primary and secondary alkyl boronic esters with diverse primary amides, including acetamide, have been developed.

Entities: Chemical Gene Species

Keywords: NacNac ligand; alkyl boronic esters; amides; copper; cross-coupling

Year: 2016 PMID： 27654642 PMCID： PMC5080986 DOI： 10.1002/chem.201603677

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

27 in total

1. Copper-mediated N-cyclopropylation of azoles, amides, and sulfonamides by cyclopropylboronic acid.

Authors: Sébastien Bénard; Luc Neuville; Jieping Zhu
Journal: J Org Chem Date: 2008-07-09 Impact factor: 4.354

2. Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.

Authors: Chanchamnan Um; Sherry R Chemler
Journal: Org Lett Date: 2016-05-10 Impact factor: 6.005

Review 3. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors: Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal: Chem Rev Date: 2011-02-14 Impact factor: 60.622

4. Diamine Ligands in Copper-Catalyzed Reactions.

Authors: David S Surry; Stephen L Buchwald
Journal: Chem Sci Date: 2010 Impact factor: 9.825

5. Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid.

Authors: Clare E Jacobson; Noelia Martinez-Muñoz; David J Gorin
Journal: J Org Chem Date: 2015-07-07 Impact factor: 4.354

Review 6. Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development.

Authors: Carlo Sambiagio; Stephen P Marsden; A John Blacker; Patrick C McGowan
Journal: Chem Soc Rev Date: 2014-03-03 Impact factor: 54.564

7. Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.

Authors: Steven A Rossi; Kirk W Shimkin; Qun Xu; Luis M Mori-Quiroz; Donald A Watson
Journal: Org Lett Date: 2013-04-23 Impact factor: 6.005

Copper-Catalyzed Amidation of Primary and Secondary Alkyl Boronic Esters.

1. Copper-mediated N-cyclopropylation of azoles, amides, and sulfonamides by cyclopropylboronic acid.

2. Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.

Review 3. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

4. Diamine Ligands in Copper-Catalyzed Reactions.

5. Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid.

Review 6. Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development.

7. Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.

8. Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2.

9. Direct stereospecific amination of alkyl and aryl pinacol boronates.

10. Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

1. A General N-alkylation Platform via Copper Metallaphotoredox and Silyl Radical Activation of Alkyl Halides.

2. Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids.

3. TBC1D21 Potentially Interacts with and Regulates Rap1 during Murine Spermatogenesis.