Fluorous Biphasic Catalysis: A Green Chemistry Concept for Alkane and Alkene Oxidation Reactions

2000 ◽  
pp. 172-181 ◽  
Author(s):  
Jean-Marc Vincent ◽  
Alain Rabion ◽  
Richard H. Fish
Keyword(s):  
Green Chemistry ◽  
Oxidation Reactions ◽  
Biphasic Catalysis ◽  
Alkene Oxidation ◽  
Fluorous Biphasic Catalysis

Fluorous biphasic catalysis. 2. Synthesis of fluoroponytailed amine ligands along with fluoroponytailed carboxylate synthons, [M(C8F17(CH2)2CO2)2] (M = Mn2+ or Co2+): Demonstration of a perfluoroheptane soluble precatalyst for alkane and alkene functionalization in the presence of tert-butyl hydroperoxide and oxygen gas

2001 ◽  
Vol 79 (5-6) ◽  
pp. 888-895 ◽  
Author(s):  
Jean-Marc Vincent ◽  
Alain Rabion ◽  
Vittal K Yachandra ◽  
Richard H Fish
Keyword(s):  
Oxidation Reactions ◽  
Biphasic Catalysis ◽  
Alkene Oxidation ◽  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
Spin Resonance ◽  
Soluble Ligand ◽  
Fluorous Biphasic Catalysis

Fluorous biphasic catalysis (FBC) is a relatively new concept for homogeneous catalysis where the fluorocarbon soluble catalyst resides in a separate phase from the substrate and products. Therefore, separation of the catalyst and the products occurs by a facile decantation process. In this contribution, we present the synthesis of new Rf-fluoroponytailed synthons, 2-iodo-1-perfluorooctyl-3-propanol (1), 3-perfluorooctyl-1-propanol (2), and 3-perfluorooctyl-1-iodopropane (3), a variety of new Rf-fluoroponytailed ligands (4–8), with starting amines, 1,4,7-triazacyclononane, bis-picolylamine, and bis-picolylaminoethylenediamine, as well as new RfMn2+ and RfCo2+ fluoroponytailed carboxylate synthons, [Mn(O2C(CH2)2C8F17)2] (9), and [Co(O2C(CH2)2C8F17)2] (10), where Rf is C8F17. The only totally perfluoralkane soluble ligand we found was 1,4,7-tris-N-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1,4,7-triazacyclononane (RfTACN, 4), and it was utilized, along with synthons 9 and 10, to generate in situ RfMn2+–RfTACN and RfCo2+–RfTACN complexes as precatalysts for functionalization of alkanes and alkenes. We will demonstrate that indeed this novel FBC approach for the separation of the precatalyst from the substrates and (or) products is viable for oxidation of alkanes and alkenes in the presence of the necessary oxidants, tert-butyl hydroperoxide (TBHP), and O2 gas. We will also show that these oxidation reactions occur via an autoxidation mechanism under our FBC conditions, while using electron spin resonance (ESR) techniques to ascertain the redox chemistry occurring with the starting mononuclear RfMn2+–RfTACN complex.Key words: fluorous solvents, biphasic catalysis, alkane/alkene oxidation.

Green Application of Phase-Transfer Catalysis in Oxidation: A Comprehensive Review

2020 ◽  
Vol 17 (4) ◽  
pp. 405-411
Author(s):  
Chuan-Hui Wang ◽  
Chen-Fu Liu ◽  
Guo-Wu Rao
Keyword(s):  
Organic Chemistry ◽  
Green Chemistry ◽  
Oxidation Reaction ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Important Application ◽  
Oxidation Reactions ◽  
Comprehensive Review ◽  
Phase Transfer Catalysts ◽  
Onium Salts

Oxidation reactions have emerged as one of the most versatile tools in organic chemistry. Various onium salts such as ammonium, phosphonium, arsonium, bismuthonium, tellurium have been used as phase transfer catalysts in many oxidation reactions. Certainly, considerable catalysts have been widely used in Phase-Transfer Catalysis (PTC). This review focuses on the application of PTC in various oxidation reaction. Furthermore, PTC also conforms to the concept of “Green Chemistry”. <p></p> • Oxidation has become one of the most widely used tools in organic chemistry and phase transfer catalysts has been widely used in oxidation. <p></p> • The application of phase transfer catalysts in oxidation reaction will be summarized. <p></p> • Phase transfer catalysts have important application in various oxidation reaction.

The Wacker Reaction and Related Alkene Oxidation Reactions

ChemInform ◽  
2003 ◽  
Vol 34 (33) ◽  
Author(s):  
James M. Takacs ◽  
Xun-tian Jiang
Keyword(s):  
Oxidation Reactions ◽  
Alkene Oxidation

Reaction Pathway Discrimination in Alkene Oxidation Reactions by Designed Ti‐Siloxy‐Polyoxometalates

ChemCatChem ◽  
2020 ◽  
Author(s):  
Teng Zhang ◽  
Albert Solé-Daura ◽  
Hugo Fouilloux ◽  
Josep M. Poblet ◽  
Anna Proust ◽  
...  
Keyword(s):  
Reaction Pathway ◽  
Oxidation Reactions ◽  
Alkene Oxidation

New bis(fluoro-ponytailed) bipyridine ligands for Pd-catalyzed Heck reactions under fluorous biphasic catalysis condition

Tetrahedron ◽  
2007 ◽  
Vol 63 (9) ◽  
pp. 2019-2023 ◽  
Author(s):  
Norman Lu ◽  
Yan-Chou Lin ◽  
Jeng-Yung Chen ◽  
Chi-Wen Fan ◽  
Ling-Kang Liu
Keyword(s):  
Heck Reactions ◽  
Biphasic Catalysis ◽  
Catalysis Condition ◽  
Fluorous Biphasic Catalysis
Sign in / Sign up

Export Citation Format

Share Document