Literature DB >> 27804289

Ligand Promoted meta-C-H Chlorination of Anilines and Phenols.

Hang Shi1, Peng Wang1, Shin Suzuki1, Marcus E Farmer1, Jin-Quan Yu1.   

Abstract

Pd-catalyzed meta-C-H chlorination of anilines and phenols is developed using norbornene as the mediator. Heterocycles, including indole, thiophene, and indazole, are tolerated. The identification of a new pyridone-based ligand is crucial for the success of this meta-C-H chlorination reaction. Subsequent diverse transformations of the chlorinated products demonstrate the versatility of meta-C-H chlorination.

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Year:  2016        PMID： 27804289      PMCID： PMC5512287          DOI： 10.1021/jacs.6b11055

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


  41 in total

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Authors:  Antonio J Martínez-Martínez; Alan R Kennedy; Robert E Mulvey; Charles T O'Hara
Journal:  Science       Date:  2014-11-14       Impact factor: 47.728

2.  Copper(II)-catalyzed meta-selective direct arylation of α-aryl carbonyl compounds.

Authors:  Hung A Duong; Ruth E Gilligan; Michael L Cooke; Robert J Phipps; Matthew J Gaunt
Journal:  Angew Chem Int Ed Engl       Date:  2010-10-22       Impact factor: 15.336

3.  Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis.

Authors:  Zhe Dong; Jianchun Wang; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2015-04-28       Impact factor: 15.419

4.  Ruthenium(II)-catalyzed C-H bond activation and functionalization.

Authors:  Percia Beatrice Arockiam; Christian Bruneau; Pierre H Dixneuf
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

5.  Palladium-Catalyzed Directed para C-H Functionalization of Phenols.

Authors:  Tuhin Patra; Sukdev Bag; Rajesh Kancherla; Anirban Mondal; Aniruddha Dey; Sandeep Pimparkar; Soumitra Agasti; Atanu Modak; Debabrata Maiti
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-09       Impact factor: 15.336

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.  meta-Selective C-H bond alkylation with secondary alkyl halides.

Authors:  Nora Hofmann; Lutz Ackermann
Journal:  J Am Chem Soc       Date:  2013-04-08       Impact factor: 15.419

8.  Ligand-enabled meta-C-H activation using a transient mediator.

Authors:  Xiao-Chen Wang; Wei Gong; Li-Zhen Fang; Ru-Yi Zhu; Suhua Li; Keary M Engle; Jin-Quan Yu
Journal:  Nature       Date:  2015-03-09       Impact factor: 49.962

9.  Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: use of a copper cocatalyst inhibits the reaction.

Authors:  Dmitri Gelman; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2003-12-15       Impact factor: 15.336

10.  Cu-Catalyzed Direct C6-Arylation of Indoles.

Authors:  Youqing Yang; Ruirui Li; Yue Zhao; Dongbing Zhao; Zhuangzhi Shi
Journal:  J Am Chem Soc       Date:  2016-07-07       Impact factor: 15.419
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  13 in total

1.  meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity.

Authors:  Luo-Yan Liu; Jennifer X Qiao; Kap-Sun Yeung; William R Ewing; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

2.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

3.  Ligand-Promoted meta-C-H Functionalization of Benzylamines.

Authors:  Peng Wang; Marcus E Farmer; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-30       Impact factor: 15.336

4.  meta-C-H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst.

Authors:  Guolin Cheng; Peng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-09       Impact factor: 15.336

5.  Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhe Dong; Gang Lu; Jianchun Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-06-27       Impact factor: 15.419

6.  meta-Selective C-H Arylation of Fluoroarenes and Simple Arenes.

Authors:  Luo-Yan Liu; Jennifer X Qiao; Kap-Sun Yeung; William R Ewing; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-09       Impact factor: 15.336

7.  Meta-Selective C-H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold.

Authors:  Qiankun Li; Eric M Ferreira
Journal:  Chemistry       Date:  2017-08-07       Impact factor: 5.236

Review 8.  Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

Authors:  Renhe Li; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2020-10-05       Impact factor: 15.419

9.  The vinylogous Catellani reaction: a combined computational and experimental study.

Authors:  Y Yamamoto; T Murayama; J Jiang; T Yasui; M Shibuya
Journal:  Chem Sci       Date:  2017-11-30       Impact factor: 9.825

10.  Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.

Authors:  Yu-Jie Wang; Chen-Hui Yuan; De-Zhao Chu; Lei Jiao
Journal:  Chem Sci       Date:  2020-09-23       Impact factor: 9.825
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