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Literature DB >> 19950911

Pd-catalyzed synthesis of allylic silanes from allylic ethers.

Ralph Moser¹, Takashi Nishikata, Bruce H Lipshutz.

Abstract

Allylic phenyl ethers serve as electrophiles toward Pd(0) en route to a variety of allylic silanes. The reactions can be run at room temperature in water as the only medium using micellar catalysis.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2010 PMID： 19950911 PMCID： PMC2804976 DOI： 10.1021/ol9023908

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

17 in total

1. Reactions in micellar systems.

Authors: Torsten Dwars; Eckhard Paetzold; Günther Oehme
Journal: Angew Chem Int Ed Engl Date: 2005-11-11 Impact factor: 15.336

2. Recent progress in Lewis base activation and control of stereoselectivity in the additions of trimethylsilyl nucleophiles.

Authors: Jacek Gawronski; Natalia Wascinska; Jadwiga Gajewy
Journal: Chem Rev Date: 2008-12 Impact factor: 60.622

3. Allylsilanes and vinylsilanes from silylcupration of carbon-carbon multiple bonds: scope and synthetic applications.

Authors: Asunción Barbero; Francisco J Pulido
Journal: Acc Chem Res Date: 2004-10 Impact factor: 22.384

4. Silylene oxonium ylides: di-tert-butylsilylene insertion into C-O bonds.

Authors: Laura E Bourque; Pamela A Haile; Janice M N Loy; K A Woerpel
Journal: Tetrahedron Date: 2009-07-11 Impact factor: 2.457

5. Cross-coupling of aromatic bromides with allylic silanolate salts.

Authors: Scott E Denmark; Nathan S Werner
Journal: J Am Chem Soc Date: 2008-12-03 Impact factor: 15.419

6. Recent advances in the activation of boron and silicon reagents for stereocontrolled allylation reactions.

Authors: Jason W J Kennedy; Dennis G Hall
Journal: Angew Chem Int Ed Engl Date: 2003-10-13 Impact factor: 15.336

7. Amination of allylic alcohols in water at room temperature.

Authors: Takashi Nishikata; Bruce H Lipshutz
Journal: Org Lett Date: 2009-06-04 Impact factor: 6.005

8. Facile and selective deallylation of allyl ethers using diphosphinidenecyclobutene-coordinated palladium catalysts.

Authors: Hiromi Murakami; Tatsuya Minami; Fumiyuki Ozawa
Journal: J Org Chem Date: 2004-06-25 Impact factor: 4.354

Review 9. Vinyl-, propargyl-, and allenylsilicon reagents in asymmetric synthesis: a relatively untapped resource of environmentally benign reagents.

Authors: Marcus J Curtis-Long; Yimon Aye
Journal: Chemistry Date: 2009 Impact factor: 5.236

10. Synthesis of (arylalkenyl)silanes by palladium-catalyzed regiospecific and stereoselective allyl transfer from silyl-substituted homoallyl alcohols to aryl halides.

Authors: Sayuri Hayashi; Koji Hirano; Hideki Yorimitsu; Koichiro Oshima
Journal: J Am Chem Soc Date: 2007-09-29 Impact factor: 15.419

6 in total

1. "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors: Bruce H Lipshutz; Subir Ghorai
Journal: Aldrichimica Acta Date: 2012-01-01 Impact factor: 3.667

2. Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature.

Authors: Bruce H Lipshutz; Subir Ghorai; Wendy Wen Yi Leong; Benjamin R Taft; Daniel V Krogstad
Journal: J Org Chem Date: 2011-05-19 Impact factor: 4.354