Literature DB >> 16599619

Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.

Zhijian Liu1, Richard C Larock.   

Abstract

An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl triflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.

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Year:  2006        PMID： 16599619      PMCID： PMC2627407          DOI： 10.1021/jo0602221

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


  31 in total

1.  An Efficient Method for Cleavage of Epoxides with Aromatic Amines.

Authors:  Govindasamy Sekar; Vinod K. Singh
Journal:  J Org Chem       Date:  1999-01-08       Impact factor: 4.354

2.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors:  Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

3.  Improved functional group compatibility in the palladium-catalyzed synthesis of aryl amines.

Authors:  Michele C Harris; Xiaohua Huang; Stephen L Buchwald
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

4.  An air and thermally stable one- component catalyst for the amination of aryl chlorides.

Authors:  Danilo Zim; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

5.  Palladium-catalyzed intermolecular coupling of aryl halides and amides.

Authors:  J Yin; S L Buchwald
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

6.  Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls.

Authors:  Zhijian Liu; Xiaoxia Zhang; Richard C Larock
Journal:  J Am Chem Soc       Date:  2005-11-16       Impact factor: 15.419

7.  N-Arylation of Sulfonamides on Solid Supports.

Authors: 
Journal:  J Comb Chem       Date:  2000-01-11

8.  A 2:1 coupling reaction of arynes with aldehydes via o-quinone methides: straightforward synthesis of 9-arylxanthenes.

Authors:  Hiroto Yoshida; Masahiko Watanabe; Hiroyuki Fukushima; Joji Ohshita; Atsutaka Kunai
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

9.  Rapid and efficient microwave-assisted amination of electron-rich aryl halides without a transition-metal catalyst.

Authors:  Lei Shi; Min Wang; Chun-An Fan; Fu-Min Zhang; Yong-Qiang Tu
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

10.  Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C[bond]C, C[bond]N, and C[bond]O bond-forming cross-couplings.

Authors:  Noriyasu Kataoka; Quinetta Shelby; James P Stambuli; John F Hartwig
Journal:  J Org Chem       Date:  2002-08-09       Impact factor: 4.354
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  25 in total

1.  An efficient computational model to predict the synthetic utility of heterocyclic arynes.

Authors:  Adam E Goetz; Sarah M Bronner; Jordan D Cisneros; Joshua M Melamed; Robert S Paton; K N Houk; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-03       Impact factor: 15.336

2.  Sulfonamide-Trapping Reactions of Thermally Generated Benzynes.

Authors:  Yuanxian Wang; Lianyou Zheng; Thomas R Hoye
Journal:  Org Lett       Date:  2018-11-05       Impact factor: 6.005

3.  Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes.

Authors:  Sarah M Bronner; Joel L Mackey; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2012-08-15       Impact factor: 15.419

4.  Quantification of the Electrophilicity of Benzyne and Related Intermediates.

Authors:  Noah F Fine Nathel; Lucas A Morrill; Herbert Mayr; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-08-09       Impact factor: 15.419

5.  Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Org Lett       Date:  2011-07-11       Impact factor: 6.005

6.  Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

7.  Indolyne and aryne distortions and nucleophilic regioselectivites.

Authors:  Paul H-Y Cheong; Robert S Paton; Sarah M Bronner; G-Yoon J Im; Neil K Garg; K N Houk
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

8.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

9.  Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-12-03       Impact factor: 4.354

10.  Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azides.

Authors:  Feng Shi; Jesse P Waldo; Yu Chen; Richard C Larock
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005
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