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Literature DB >> 21384889

Base-mediated intermolecular sp2 C-H bond arylation via benzyne intermediates.

Abstract

A transition-metal-free method for arylation of heterocycle and arene carbon-hydrogen bonds by aryl chlorides and fluorides has been developed. The reactions proceed via aryne intermediates and are highly regioselective with respect to the C-H bond coupling component.

Entities: Chemical Disease Species

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Year: 2011 PMID： 21384889 PMCID： PMC3065930 DOI： 10.1021/ja200184b

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

37 in total

1. 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

Review 2. 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

3. Modulating reactivity and diverting selectivity in palladium-catalyzed heteroaromatic direct arylation through the use of a chloride activating/blocking group.

Authors: Benoît Liégault; Ivan Petrov; Serge I Gorelsky; Keith Fagnou
Journal: J Org Chem Date: 2010-02-19 Impact factor: 4.354

4. Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

Authors: G-Yoon J Im; Sarah M Bronner; Adam E Goetz; Robert S Paton; Paul H-Y Cheong; K N Houk; Neil K Garg
Journal: J Am Chem Soc Date: 2010-11-29 Impact factor: 15.419

5. A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C-H bond cleavage.

Authors: Fumitoshi Kakiuchi; Shintaro Kan; Kimitaka Igi; Naoto Chatani; Shinji Murai
Journal: J Am Chem Soc Date: 2003-02-19 Impact factor: 15.419

6. Palladium-catalyzed cross-coupling of pyrrole anions with aryl chlorides, bromides, and iodides.

Authors: Ryan D Rieth; Neal P Mankad; Elisa Calimano; Joseph P Sadighi
Journal: Org Lett Date: 2004-10-28 Impact factor: 6.005

7. Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors: Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal: J Am Chem Soc Date: 2008-06-27 Impact factor: 15.419

8. Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines.

Authors: Sirilata Yotphan; Robert G Bergman; Jonathan A Ellman
Journal: Org Lett Date: 2009-04-02 Impact factor: 6.005

9. Two methods for direct ortho-arylation of benzoic acids.

Authors: Hendrich A Chiong; Quynh-Nhu Pham; Olafs Daugulis
Journal: J Am Chem Soc Date: 2007-07-25 Impact factor: 15.419

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

11 in total

1. Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates.

Authors: Milad Mesgar; Olafs Daugulis
Journal: Org Lett Date: 2017-07-28 Impact factor: 6.005

2. Direct intermolecular aniline ortho-arylation via benzyne intermediates.

Authors: Thanh Truong; Olafs Daugulis
Journal: Org Lett Date: 2012-11-13 Impact factor: 6.005

3. Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols.

Authors: Thanh Truong; Olafs Daugulis
Journal: Chem Sci Date: 2013 Impact factor: 9.825

4. Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides.

Authors: Ji Chen; Jimmy Wu
Journal: Angew Chem Int Ed Engl Date: 2017-03-03 Impact factor: 15.336

5. Transition-metal-free alkynylation of aryl chlorides.

Authors: Thanh Truong; Olafs Daugulis
Journal: Org Lett Date: 2011-07-25 Impact factor: 6.005

6. Pd(II)-catalyzed ortho arylation of 2-arylbenzothiazoles with aryl iodides via benzothiazole-directed C-H activation.

Authors: Qiuping Ding; Huafang Ji; Dan Wang; Yuqing Lin; Weihua Yu; Yiyuan Peng
Journal: J Organomet Chem Date: 2012-07-15 Impact factor: 2.369

7. Room-Temperature Direct β-Arylation of Thiophenes and Benzo[b]thiophenes and Kinetic Evidence for a Heck-type Pathway.

Authors: Chiara Colletto; Saidul Islam; Francisco Juliá-Hernández; Igor Larrosa
Journal: J Am Chem Soc Date: 2016-01-28 Impact factor: 15.419