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Literature DB >> 23148679

Direct intermolecular aniline ortho-arylation via benzyne intermediates.

Abstract

A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of enantiopure binaphthyldiamine affords a product with >99% ee.

Entities: Chemical Species

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Year: 2012 PMID： 23148679 PMCID： PMC3518720 DOI： 10.1021/ol302875x

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

26 in total

1. Selective transition state stabilization via hyperconjugative and conjugative assistance: stereoelectronic concept for copper-free click chemistry.

Authors: Brian Gold; Nikolay E Shevchenko; Natalie Bonus; Gregory B Dudley; Igor V Alabugin
Journal: J Org Chem Date: 2011-12-07 Impact factor: 4.354

2. Anilide ortho-arylation by using C-H activation methodology.

Authors: Olafs Daugulis; Vladimir G Zaitsev
Journal: Angew Chem Int Ed Engl Date: 2005-06-27 Impact factor: 15.336

Review 3. 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

4. Steric modulation of chiral biaryl diamines via Pd-catalyzed directed C-H arylation.

Authors: Christopher C Scarborough; Richard I McDonald; Caroline Hartmann; Graham T Sazama; Ana Bergant; Shannon S Stahl
Journal: J Org Chem Date: 2009-03-20 Impact factor: 4.354

5. Twofold C-H functionalization: palladium-catalyzed ortho arylation of anilides.

Authors: Gordon Brasche; Jorge García-Fortanet; Stephen L Buchwald
Journal: Org Lett Date: 2008-05-09 Impact factor: 6.005

6. Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

Authors: Dipannita Kalyani; Nicholas R Deprez; Lopa V Desai; Melanie S Sanford
Journal: J Am Chem Soc Date: 2005-05-25 Impact factor: 15.419

7. Palladium-catalyzed anilide ortho-arylation and subsequent one-pot cyclization to phenanthridines.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Org Chem Date: 2007-09-07 Impact factor: 4.354

8. Synthesis of amino- and hydroxybiphenyls by radical chain reaction of arenediazonium salts.

Authors: Alexander Wetzel; Varinia Ehrhardt; Markus R Heinrich
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

9. TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines.

Authors: Chunhui Huang; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2009-08-12 Impact factor: 15.419