Literature DB >> 16277509

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

Zhijian Liu1, Xiaoxia Zhang, Richard C Larock.   

Abstract

The Pd-catalyzed annulation of arynes by 2-halobiaryls and related vinylic halides provides a very efficient, high yielding synthesis of polycyclic aromatic and heteroaromatic hydrocarbons. This process appears to involve the catalytic, stepwise coupling of two very reactive substrates, an aryne and an organopalladium species, to generate excellent yields of cross-coupled products.

Entities:  

Year:  2005        PMID: 16277509     DOI: 10.1021/ja055781o

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


  17 in total

1.  Pd(OAc)(2)-catalyzed Domino reactions of 1-chloro-2-haloarenes and 2-haloaryl tosylates with hindered Grignard reagents via palladium-associated arynes.

Authors:  Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

2.  Highly efficient route to fused polycyclic aromatics via palladium-catalyzed aryne annulation by aryl halides.

Authors:  Zhijian Liu; Richard C Larock
Journal:  J Org Chem       Date:  2007-01-05       Impact factor: 4.354

3.  Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.

Authors:  Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-09-26       Impact factor: 4.354

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

Authors:  Zhijian Liu; Richard C Larock
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

5.  Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.

Authors:  Yuesi Fang; Chunrui Wu; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2011-10-12       Impact factor: 4.354

6.  Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines.

Authors:  Arif Kivrak; Richard C Larock
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

7.  Synthesis of 9-fluorenylidenes and 9,10-phenanthrenes through palladium-catalyzed aryne annulation by o-halostyrenes and o-halo allylic benzenes.

Authors:  Shilpa A Worlikar; Richard C Larock
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

8.  Pd(OAc)(2)-catalyzed domino reactions of 1,2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes.

Authors:  Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Tetrahedron       Date:  2008-03-10       Impact factor: 2.457

9.  Efficient synthesis of fluoren-9-ones by the palladium-catalyzed annulation of arynes by 2-haloarenecarboxaldehydes.

Authors:  Jesse P Waldo; Xiaoxia Zhang; Feng Shi; Richard C Larock
Journal:  J Org Chem       Date:  2008-08-07       Impact factor: 4.354

10.  Palladium-catalyzed synthesis of 9-fluorenylidenes through aryne annulation.

Authors:  Shilpa A Worlikar; Richard C Larock
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

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