Literature DB >> 28617611

Palladium Catalyzed Arylation and Benzylation of Nitroarenes Using Aryl Sulfonates and Benzyl Acetates.

Zubaoyi Yi1, Yodit Aschenaki1, Ryan Daley1, Stephen Davick1, Abigail Schnaith1, Rylee Wander1, Dipannita Kalyani1.   

Abstract

Pd-catalyzed arylation or benzylation of nitroazoles using aryl sulfonates or benzyl acetates is described. Electronically varied aryl tosylates and mesylates, as well as benzyl acetates, afford the arylated and benzylated products. Arylation of nitrobenzene is also reported. The relative rate for the arylation of halides is greater than that of tosylates using the reported reaction parameters. These studies enhance the scope of electrophiles for nitroarene arylations and benzylations, which was hitherto limited to the use of halide electrophiles.

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Year:  2017        PMID: 28617611      PMCID: PMC5679234          DOI: 10.1021/acs.joc.7b00550

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


  37 in total

Review 1.  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

2.  Catalytic arylation reactions by C-H bond activation with aryl tosylates.

Authors:  Lutz Ackermann; Andreas Althammer; Robert Born
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-10       Impact factor: 15.336

3.  Palladium-catalyzed direct arylations of heteroarenes with tosylates and mesylates.

Authors:  Lutz Ackermann; Andreas Althammer; Sabine Fenner
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 4.  Recent advances in aryl-aryl bond formation by direct arylation.

Authors:  Gerard P McGlacken; Lorraine M Bateman
Journal:  Chem Soc Rev       Date:  2009-05-22       Impact factor: 54.564

Review 5.  Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage.

Authors:  Lutz Ackermann; Rubén Vicente; Anant R Kapdi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Palladium-catalyzed direct arylation of nitro-substituted aromatics with aryl halides.

Authors:  Laurence Caron; Louis-Charles Campeau; Keith Fagnou
Journal:  Org Lett       Date:  2008-09-24       Impact factor: 6.005

7.  N,N-diethyl O-carbamate: directed metalation group and orthogonal Suzuki-Miyaura cross-coupling partner.

Authors:  Aurora Antoft-Finch; Tom Blackburn; Victor Snieckus
Journal:  J Am Chem Soc       Date:  2009-12-16       Impact factor: 15.419

8.  Palladium-catalyzed direct arylations, alkenylations, and benzylations through C-H bond cleavages with sulfamates or phosphates as electrophiles.

Authors:  Lutz Ackermann; Sebastian Barfüsser; Jola Pospech
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

Review 9.  Palladium-catalyzed ligand-directed C-H functionalization reactions.

Authors:  Thomas W Lyons; Melanie S Sanford
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

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

Authors:  Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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