Literature DB >> 16119945

Palladium-catalyzed annulation of arynes by 2-halobenzaldehydes: synthesis of fluoren-9-ones.

Xiaoxia Zhang1, Richard C Larock.   

Abstract

Arynes, generated in situ from 2-(trimethylsilyl)aryl triflates and CsF, undergo annulation by o-haloarenecarboxaldehydes in the presence of a Pd catalyst, providing a useful new method for the synthesis of fluoren-9-ones in good yields. [reaction: see text]

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Year:  2005        PMID： 16119945     DOI： 10.1021/ol0514597

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


  11 in total

1.  Fluorenone synthesis by palladacycle-catalyzed sequential reactions of 2-bromobenzaldehydes with arylboronic acids.

Authors:  Tao-Ping Liu; Yuan-Xi Liao; Chun-Hui Xing; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2011-04-11       Impact factor: 6.005

2.  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

3.  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

4.  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

5.  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

6.  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

7.  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

8.  Carbon-hydrogen bond functionalization approach for the synthesis of fluorenones and ortho-arylated benzonitriles.

Authors:  Dmitry Shabashov; Jesús R Molina Maldonado; Olafs Daugulis
Journal:  J Org Chem       Date:  2008-09-03       Impact factor: 4.354

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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