Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Arylation of rhodium(II) azavinyl carbenes with boronic acids.

Literature DB >> 22913576

Arylation of rhodium(II) azavinyl carbenes with boronic acids.

Nicklas Selander¹, Brady T Worrell, Stepan Chuprakov, Subash Velaparthi, Valery V Fokin.

Abstract

A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized into substituted indoles employing copper catalysis.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2012 PMID： 22913576 PMCID： PMC3597238 DOI： 10.1021/ja3062453

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

33 in total

1. Recent Advances in Asymmetric Catalytic Metal Carbene Transformations.

Authors: Michael P. Doyle; David C. Forbes
Journal: Chem Rev Date: 1998-04-02 Impact factor: 60.622

2. Cascade Processes of Metallo Carbenoids.

Authors: Albert Padwa; M. David Weingarten
Journal: Chem Rev Date: 1996-02-01 Impact factor: 60.622

Review 3. Practical methodologies for the synthesis of indoles.

Authors: Guy R Humphrey; Jeffrey T Kuethe
Journal: Chem Rev Date: 2006-07 Impact factor: 60.622

4. Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.

Authors: Stepan Chuprakov; Frank W Hwang; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. Diamine Ligands in Copper-Catalyzed Reactions.

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

6. Arylation of α-chiral ketones by palladium-catalyzed cross-coupling reactions of tosylhydrazones with aryl halides.

Authors: José Barluenga; María Escribano; Fernando Aznar; Carlos Valdés
Journal: Angew Chem Int Ed Engl Date: 2010-09-10 Impact factor: 15.336

7. Tosylhydrazones: new uses for classic reagents in palladium-catalyzed cross-coupling and metal-free reactions.

Authors: José Barluenga; Carlos Valdés
Journal: Angew Chem Int Ed Engl Date: 2011-07-11 Impact factor: 15.336

8. Metal-free carbon-carbon bond-forming reductive coupling between boronic acids and tosylhydrazones.

Authors: José Barluenga; María Tomás-Gamasa; Fernando Aznar; Carlos Valdés
Journal: Nat Chem Date: 2009-08-16 Impact factor: 24.427

9. Synthesis and reactivity of rhodium(II) N-triflyl azavinyl carbenes.

Authors: Neil Grimster; Li Zhang; Valery V Fokin
Journal: J Am Chem Soc Date: 2010-03-03 Impact factor: 15.419

10. Arylation and vinylation of alpha-diazocarbonyl compounds with boroxines.

Authors: Cheng Peng; Wei Zhang; Guobing Yan; Jianbo Wang
Journal: Org Lett Date: 2009-04-02 Impact factor: 6.005

16 in total

1. Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight.

Authors: Shea L Johnson; Michael K Hilinski
Journal: J Org Chem Date: 2019-06-19 Impact factor: 4.354

2. Rhodium-Catalyzed Intermolecular C-H Functionalization as a Key Step in the Synthesis of Complex Stereodefined β-Arylpyrrolidines.

Authors: Robert W Kubiak; Huw M L Davies
Journal: Org Lett Date: 2018-06-21 Impact factor: 6.005

3. Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles.

Authors: Anton V Gulevich; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2013-01-07 Impact factor: 15.336

4. Ring expansion and rearrangements of rhodium(II) azavinyl carbenes.

Authors: Nicklas Selander; Brady T Worrell; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2012-11-19 Impact factor: 15.336

5. Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

Authors: Sen Wai Kwok; Li Zhang; Neil P Grimster; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2014-03-24 Impact factor: 15.336

6. Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

Authors: Yi Shi; Anton V Gulevich; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2014-10-21 Impact factor: 15.336

10. Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: synthesis of 4-haloisoxazoles and 5-halotriazoles.

Authors: James S Oakdale; Rakesh K Sit; Valery V Fokin
Journal: Chemistry Date: 2014-07-24 Impact factor: 5.236