Fluorous chemistry without fluorous solvents: New catalyst recovery protocols based upon fluoropolymers

ORGN 209

John A. Gladysz, gladysz@organik.uni-erlangen.de, Institut für Organische Chemie, Universität Erlangen-Nürnberg, Henkestraße 42, Erlangen, 91054, Germany
Conventional fluorous catalysis exploits the temperature-dependent miscibilities of fluorous and organic solvents. Reactions are often conducted at the high-temperature, one phase limit, with product/catalyst separation at the low-temperature, two-phase limit. Catalysts are functionalized with "pony tails" of the formula (CH2)m(CF2)n-1CF3, which in sufficient length and number ensure high fluorous phase affinities. This talk will focus on recent efforts to eliminate the fluorous solvent requirement. We have found that many fluorous compounds exhibit highly temperature dependent solubilities in organic solvents. Such "thermomorphic" behavior allows fluorous catalysts to be utilized under one phase conditions at elevated temperatures in ordinary organic solvents, and recovered by a simple liquid/solid phase separation at low temperature. It is advantageous to conduct these reactions in the presence of a fluorous support, especially when catalyst quantities are small. This talk will highlight recent refinements involve fluoropolymers such as Teflon. Rhodium-catalyzed hydrosilylations and ruthenium-catalyzed alkene metatheses will be emphasized.

 

Recent Advances in Fluorous Chemistry
8:00 AM-12:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Ballroom C, Oral

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005