Literature DB >> 19243177

Palladium-catalyzed C-H bond functionalization with arylsulfonyl chlorides.

Xiaodan Zhao1, Elena Dimitrijević, Vy M Dong.   

Abstract

Selective C-H bond functionalization enables efficient access to valuable products from relatively simple precursors and thus remains a longstanding challenge in organic synthesis. This communication highlights the discovery of arylsulfonyl chlorides as readily available, inexpensive, and versatile reagents for C-H bond functionalization. A novel Pd-catalyzed synthesis of arylsulfones that features a rare C-H bond activation/functionalization to form a C-S bond is presented. By simple alterations of the reaction parameters, Pd-catalyzed C-Cl and C-C bond formation can also be achieved using arylsulfonyl chlorides as the oxidant.

Entities:  

Year:  2009        PMID: 19243177     DOI: 10.1021/ja900200g

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


  28 in total

1.  On the mechanism of palladium-catalyzed aromatic C-H oxidation.

Authors:  David C Powers; Daphne Y Xiao; Matthias A L Geibel; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

2.  Rh-Catalyzed decarbonylative coupling with alkynes via C-C activation of isatins.

Authors:  Rong Zeng; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2015-01-15       Impact factor: 15.419

3.  Pd(II)-catalyzed C-H iodination using molecular I2 as the sole oxidant.

Authors:  Xiao-Chen Wang; Yi Hu; Samuel Bonacorsi; Yang Hong; Richard Burrell; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-07-09       Impact factor: 15.419

Review 4.  Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors:  Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-24       Impact factor: 15.336

5.  Controlling site selectivity in palladium-catalyzed C-H bond functionalization.

Authors:  Sharon R Neufeldt; Melanie S Sanford
Journal:  Acc Chem Res       Date:  2012-05-03       Impact factor: 22.384

6.  Ligand-accelerated C-H activation reactions: evidence for a switch of mechanism.

Authors:  Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  Copper-catalyzed ortho-acylation of phenols with aryl aldehydes and its application in one-step preparation of xanthones.

Authors:  Jun Hu; Enoch A Adogla; Yong Ju; Daping Fan; Qian Wang
Journal:  Chem Commun (Camb)       Date:  2012-10-15       Impact factor: 6.222

8.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837

9.  Mechanistic comparison between Pd-catalyzed ligand-directed C-H chlorination and C-H acetoxylation.

Authors:  Kara J Stowers; Melanie S Sanford
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

Review 10.  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

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