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Literature DB >> 24433154

Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature.

Stefan R K Minkler¹, Nicholas A Isley, Daniel J Lippincott, Norbert Krause, Bruce H Lipshutz.

Abstract

The first examples of gold-catalyzed cyclizations of diols and triols to the corresponding hetero- or spirocycles in an aqueous medium are presented. These reactions take place within nanomicelles, where the hydrophobic effect is operating, thereby driving the dehydrations, notwithstanding the surrounding water. By the addition of simple salts such as sodium chloride, reaction times and catalyst loadings can be significantly decreased.

Entities: Chemical Species

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Year: 2014 PMID： 24433154 PMCID： PMC4219360 DOI： 10.1021/ol403402h

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

17 in total

1. Formal total synthesis of okadaic acid via regiocontrolled gold(I)-catalyzed spiroketalizations.

Authors: Chao Fang; Yucheng Pang; Craig J Forsyth
Journal: Org Lett Date: 2010-10-15 Impact factor: 6.005

2. Heck couplings at room temperature in nanometer aqueous micelles.

Authors: Bruce H Lipshutz; Benjamin R Taft
Journal: Org Lett Date: 2008-03-12 Impact factor: 6.005

3. Allylic ethers as educts for Suzuki-Miyaura couplings in water at room temperature.

Authors: Takashi Nishikata; Bruce H Lipshutz
Journal: J Am Chem Soc Date: 2009-09-02 Impact factor: 15.419

4. Gold catalysis in micellar systems.

Authors: Stefan R K Minkler; Bruce H Lipshutz; Norbert Krause
Journal: Angew Chem Int Ed Engl Date: 2011-07-01 Impact factor: 15.336

5. Gold catalysis in organic synthesis: efficient cycloisomerization of alpha-aminoallenes to 3-pyrrolines.

Authors: Nobuyoshi Morita; Norbert Krause
Journal: Org Lett Date: 2004-10-28 Impact factor: 6.005

6. An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.

Authors: Aaron Aponick; Chuan-Ying Li; Jeremy Malinge; Emerson Finco Marques
Journal: Org Lett Date: 2009-10-15 Impact factor: 6.005

7. Zn-mediated, Pd-catalyzed cross-couplings in water at room temperature without prior formation of organozinc reagents.

Authors: Arkady Krasovskiy; Christophe Duplais; Bruce H Lipshutz
Journal: J Am Chem Soc Date: 2009-11-04 Impact factor: 15.419

8. Dehydration reactions in water. Brønsted Acid-surfactant-combined catalyst for ester, ether, thioether, and dithioacetal formation in water.

Authors: Kei Manabe; Shinya Iimura; Xiang-Min Sun; Shū Kobayashi
Journal: J Am Chem Soc Date: 2002-10-09 Impact factor: 15.419

Review 5. Nanoreactors for green catalysis.

Authors: M Teresa De Martino; Loai K E A Abdelmohsen; Floris P J T Rutjes; Jan C M van Hest
Journal: Beilstein J Org Chem Date: 2018-03-29 Impact factor: 2.883

5 in total

Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature.

1. Formal total synthesis of okadaic acid via regiocontrolled gold(I)-catalyzed spiroketalizations.

2. Heck couplings at room temperature in nanometer aqueous micelles.

3. Allylic ethers as educts for Suzuki-Miyaura couplings in water at room temperature.

4. Gold catalysis in micellar systems.

5. Gold catalysis in organic synthesis: efficient cycloisomerization of alpha-aminoallenes to 3-pyrrolines.

6. An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.

7. Zn-mediated, Pd-catalyzed cross-couplings in water at room temperature without prior formation of organozinc reagents.

8. Dehydration reactions in water. Brønsted Acid-surfactant-combined catalyst for ester, ether, thioether, and dithioacetal formation in water.

Review 9. On the way towards greener transition-metal-catalyzed processes as quantified by E factors.

10. C-C bond formation via copper-catalyzed conjugate addition reactions to enones in water at room temperature.

1. Transitioning organic synthesis from organic solvents to water. What's your E Factor?

2. A versatile route to polythiophenes with functional pendant groups using alkyne chemistry.

3. A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds.

4. Micellar catalysis-enabled sustainable ppm Au-catalyzed reactions in water at room temperature.

Review 5. Nanoreactors for green catalysis.