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Literature DB >> 24616243

Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature.

Sachin Handa¹, James C Fennewald, Bruce H Lipshutz.

Abstract

On the basis of the far higher solubility of oxygen gas inside the hydrocarbon core of nanomicelles, metal and peroxide free aerobic oxidation of aryl alkynes to β-ketosulfones has been achieved in water at room temperature. Many examples are offered that illustrate broad functional group tolerance. The overall process is environmentally friendly, documented by the associated low E Factors.

Entities: Chemical Gene

Keywords: E Factor; TPGS-750-M; aerobic oxidation; hydrophobic effect; micellar catalysis

Mesh：

Substances：
Alkynes
Water

Year: 2014 PMID： 24616243 PMCID： PMC4076018 DOI： 10.1002/anie.201310634

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

14 in total

1. Tandem Reactions in Organic Synthesis: Novel Strategies for Natural Product Elaboration and the Development of New Synthetic Methodology.

Authors: Philip J. Parsons; Clive S. Penkett; Adrian J. Shell
Journal: Chem Rev Date: 1996-02-01 Impact factor: 60.622

2. "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

Review 3. Hydrophobically directed organic synthesis.

Authors: Ulf M Lindström; Fredrik Andersson
Journal: Angew Chem Int Ed Engl Date: 2006-01-16 Impact factor: 15.336

4. Aerobic oxysulfonylation of alkenes leading to secondary and tertiary β-hydroxysulfones.

Authors: Qingquan Lu; Jian Zhang; Fuliang Wei; Yue Qi; Huamin Wang; Zhiliang Liu; Aiwen Lei
Journal: Angew Chem Int Ed Engl Date: 2013-05-23 Impact factor: 15.336

5. Rapid synthesis of sulfone derivatives as potential anti-infectious agents.

Authors: C Curti; M Laget; A Ortiz Carle; A Gellis; P Vanelle
Journal: Eur J Med Chem Date: 2007-01-09 Impact factor: 6.514

6. TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

Authors: Bruce H Lipshutz; Subir Ghorai; Alexander R Abela; Ralph Moser; Takashi Nishikata; Christophe Duplais; Arkady Krasovskiy; Ricky D Gaston; Robert C Gadwood
Journal: J Org Chem Date: 2011-05-09 Impact factor: 4.354

7. Synthesis and biological evaluation of sulfonamidooxazoles and beta-keto sulfones: selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.

Authors: Jason Xiang; Manus Ipek; Vipin Suri; Walt Massefski; Ning Pan; Ying Ge; May Tam; Yuzhe Xing; James F Tobin; Xin Xu; Steve Tam
Journal: Bioorg Med Chem Lett Date: 2005-06-02 Impact factor: 2.823

8. Copper-catalyzed direct oxysulfonylation of alkenes with dioxygen and sulfonylhydrazides leading to β-ketosulfones.

Authors: Wei Wei; Chunli Liu; Daoshan Yang; Jiangwei Wen; Jinmao You; Yourui Suo; Hua Wang
Journal: Chem Commun (Camb) Date: 2013-11-11 Impact factor: 6.222

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

Authors: Bruce H Lipshutz; Nicholas A Isley; James C Fennewald; Eric D Slack
Journal: Angew Chem Int Ed Engl Date: 2013-09-12 Impact factor: 15.336

10. Transforming Suzuki-Miyaura cross-couplings of MIDA boronates into a green technology: no organic solvents.

Authors: Nicholas A Isley; Fabrice Gallou; Bruce H Lipshutz
Journal: J Am Chem Soc Date: 2013-11-13 Impact factor: 15.419

4 in total

Review 1. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.

Authors: Raju Jannapu Reddy; Arram Haritha Kumari
Journal: RSC Adv Date: 2021-03-01 Impact factor: 3.361

Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature.

1. Tandem Reactions in Organic Synthesis: Novel Strategies for Natural Product Elaboration and the Development of New Synthetic Methodology.

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

Review 3. Hydrophobically directed organic synthesis.

4. Aerobic oxysulfonylation of alkenes leading to secondary and tertiary β-hydroxysulfones.

5. Rapid synthesis of sulfone derivatives as potential anti-infectious agents.

6. TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

7. Synthesis and biological evaluation of sulfonamidooxazoles and beta-keto sulfones: selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.

8. Copper-catalyzed direct oxysulfonylation of alkenes with dioxygen and sulfonylhydrazides leading to β-ketosulfones.

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

10. Transforming Suzuki-Miyaura cross-couplings of MIDA boronates into a green technology: no organic solvents.

Review 1. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.

Review 2. Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones.

3. Designer Micelles Accelerate Flux Through Engineered Metabolism in E. coli and Support Biocompatible Chemistry.

4. K₂S₂O₈-Promoted Aryl Thioamides Synthesis from Aryl Aldehydes Using Thiourea as the Sulfur Source.

Review 3. Hydrophobically directed organic synthesis.

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

Review 1. Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds.

Review 2. Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones.

Review 1. Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds.