Literature DB >> 20092358

Arylchlorogermanes/TBAF/"moist" toluene: a promising combination for Pd-catalyzed Germyl-Stille cross-coupling.

Zun-Ting Zhang1, Jean-Philippe Pitteloud, Laura Cabrera, Yong Liang, Myrdich Toribio, Stanislaw F Wnuk.   

Abstract

The trichlorophenyl,- dichlorodiphenyl,- and chlorotriphenylgermanes undergo Pd-catalyzed cross-couplings with aryl bromides and iodides in the presence of TBAF in toluene with addition of the measured amount of water. One chloride ligand on the Ge center allows efficient activation by fluoride to promote transfer of one, two, or three phenyl groups from the organogermane precursors.

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Year:  2010        PMID： 20092358      PMCID： PMC2827299          DOI： 10.1021/ol9028918

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


  14 in total

1.  Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates.

Authors:  Scott E Denmark; Ramzi F Sweis
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

2.  Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates.

Authors:  G A Grasa; S P Nolan
Journal:  Org Lett       Date:  2001-01-11       Impact factor: 6.005

3.  Coupling of 2-Substituted 1-Fluorovinylstannanes with Organic Halides Catalyzed by Palladium(0)/Copper(I) Iodide. A Mild and Stereospecific Method to Monofluoroolefins.

Authors:  Chen Chen; Keith Wilcoxen; Yun-Fei Zhu; James R. McCarthy
Journal:  J Org Chem       Date:  1999-05-14       Impact factor: 4.354

4.  Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis.

Authors:  Scott E Denmark; Ramzi F Sweis
Journal:  J Am Chem Soc       Date:  2004-04-21       Impact factor: 15.419

5.  Fluoride-promoted cross-coupling reactions of alkenylsilanols. Elucidation of the mechanism through spectroscopic and kinetic analysis.

Authors:  Scott E Denmark; Ramzi F Sweis; Daniel Wehrli
Journal:  J Am Chem Soc       Date:  2004-04-21       Impact factor: 15.419

6.  Biaryl synthesis from two different aryl halides with tri(2-furyl)germane.

Authors:  Tomoaki Nakamura; Hidenori Kinoshita; Hiroshi Shinokubo; Koichiro Oshima
Journal:  Org Lett       Date:  2002-09-05       Impact factor: 6.005

7.  Cross-coupling reactions of (1-fluorovinyl)methydiphenylsilane(1) with aryl halides and aryl triflates.

Authors:  Takeshi Hanamoto; Tomoko Kobayashi
Journal:  J Org Chem       Date:  2003-08-08       Impact factor: 4.354

8.  Preparation and palladium-catalyzed cross-coupling of aryl triethylammonium bis(catechol) silicates with aryl triflates.

Authors:  W Michael Seganish; Philip DeShong
Journal:  J Org Chem       Date:  2004-02-20       Impact factor: 4.354

9.  Light-fluorous safety-catch arylgermanes - exceptionally robust, photochemically activated precursors for biaryl synthesis by Pd(0) catalysed cross-coupling.

Authors:  Alan C Spivey; Chih-Chung Tseng; Joseph P Hannah; Christopher J G Gripton; Paul de Fraine; Nigel J Parr; Jan J Scicinski
Journal:  Chem Commun (Camb)       Date:  2007-06-21       Impact factor: 6.222

10.  Pd(PPh3)4-PEG 400 catalyzed protocol for the atom-efficient Stille cross-coupling reaction of organotin with aryl bromides.

Authors:  Wen-Jun Zhou; Ke-Hu Wang; Jin-Xian Wang
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354
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  2 in total

1.  Fluoride-promoted cross-coupling of chloro(mono-, di-, or triphenyl)germanes with aryl halides in "moist" toluene. Multiple transfer of the phenyl group from organogermane substrates and comparison of the coupling efficiencies of chloro(phenyl)germanes with their corresponding stannane and silane counterparts.

Authors:  Jean-Philippe Pitteloud; Zun-Ting Zhang; Yong Liang; Laura Cabrera; Stanislaw F Wnuk
Journal:  J Org Chem       Date:  2010-11-10       Impact factor: 4.354

2.  Gold-Catalyzed C-H Functionalization with Aryl Germanes.

Authors:  Christoph Fricke; Amit Dahiya; William B Reid; Franziska Schoenebeck
Journal:  ACS Catal       Date:  2019-08-30       Impact factor: 13.084
  2 in total

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