Literature DB >> 16388678

Expedited palladium-catalyzed amination of aryl nonaflates through the use of microwave-irradiation and soluble organic amine bases.

Rachel E Tundel1, Kevin W Anderson, Stephen L Buchwald.   

Abstract

[reaction: see text] Microwave-assisted, palladium-catalyzed C-N bond-forming reactions with aryl/heteroaryl nonaflates and amines using the soluble amine bases DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or MTBD (7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene) and ligands (1-3) resulted in good to excellent yields (71-99%) of arylamines in short reaction times (1-45 min).

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Year:  2006        PMID： 16388678     DOI： 10.1021/jo052131u

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  13 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

2.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

3.  Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling.

Authors:  Joseph M Dennis; Nicholas A White; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-03-22       Impact factor: 15.419

Review 4.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

6.  Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles.

Authors:  Xiang Wang; Denis V Gribkov; Dalibor Sames
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

7.  Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis.

Authors:  Nicholas A Isley; Sebastian Dobarco; Bruce H Lipshutz
Journal:  Green Chem       Date:  2014-01-02       Impact factor: 10.182

Review 8.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

9.  Bright Side of Lignin Depolymerization: Toward New Platform Chemicals.

Authors:  Zhuohua Sun; Bálint Fridrich; Alessandra de Santi; Saravanakumar Elangovan; Katalin Barta
Journal:  Chem Rev       Date:  2018-01-16       Impact factor: 60.622

10.  Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide.

Authors:  Holly McErlain; Leanne M Riley; Andrew Sutherland
Journal:  J Org Chem       Date:  2021-11-02       Impact factor: 4.354
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