Literature DB >> 16268609

Kumada coupling of aryl and vinyl tosylates under mild conditions.

Michael E Limmert1, Amy H Roy, John F Hartwig.   

Abstract

[Reaction: see text]. Aryl and alkenyl tosylates are easily prepared, inexpensive and, thus, attractive for transition-metal-catalyzed couplings, but their reactivity is low. We report examples of mild, palladium-catalyzed coupling of aryl, alkenyl, and alkyl Grignard reagents with aryl and alkenyl tosylates. The resulting biaryls, vinylarenes, and alkylarenes were isolated in good to excellent yield. These couplings were conducted with a nearly equimolar ratio of the two reactants, and many examples were conducted at room temperature.

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Year:  2005        PMID: 16268609     DOI: 10.1021/jo051394l

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  11 in total

Review 1.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

2.  Ligand effects on Negishi couplings of alkenyl halides.

Authors:  Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

3.  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

4.  Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.

Authors:  Kyle W Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L Silberstein; Anna Komaromi; Tom Blackburn; Stephen D Ramgren; K N Houk; Victor Snieckus; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-04-01       Impact factor: 15.419

5.  Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature.

Authors:  Tokutaro Ogata; John F Hartwig
Journal:  J Am Chem Soc       Date:  2008-09-24       Impact factor: 15.419

6.  (E)-1,2-Diphenyl-ethenyl methane-sulfonate.

Authors:  Yonghua Feng; Liu Ying; Chen Zhang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-24

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.  Nickel-catalyzed Suzuki-Miyaura couplings in green solvents.

Authors:  Stephen D Ramgren; Liana Hie; Yuxuan Ye; Neil K Garg
Journal:  Org Lett       Date:  2013-07-23       Impact factor: 6.005

9.  Rapid Room-Temperature, Chemoselective Csp2 -Csp2 Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air.

Authors:  Indrek Kalvet; Guillaume Magnin; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-29       Impact factor: 15.336

Review 10.  Synthesis of Tetrabenazine and Its Derivatives, Pursuing Efficiency and Selectivity.

Authors:  Seung-Mann Paek
Journal:  Molecules       Date:  2020-03-05       Impact factor: 4.411

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