Fluorous Synthesis of Heterocyclic Systems

Abstract

and Ph.D. in 1993 from the University of Pittsburgh under the direction of the late Professor Paul Dowd. After a two-year stay at the same university as a Research Assistant Professor, he joined DuPont in 1995. In early 2001 he moved back to Pittsburgh and was one of the key founding members of Fluorous Technologies, Inc. (FTI). He is now the Director of Discovery Chemistry responsible for the research and development of fluorous technologies for solution-phase synthesis and separations. Over the years, Dr. Zhang has gained both academic and industrial experience. His professional areas of interest include free radical chemistry, heterocyclic chemistry, fluorous chemistry, microwave-assisted organic synthesis, and design and synthesis of drug-like small molecule libraries. He has published over 50 peer-reviewed papers including 2 book chapters and 6 review articles. In recent years he delivered many invited lectures and international conference presentations on fluorous technologies and combinatorial chemistry.

Solution‐, Solid‐Phase, and Fluorous Synthesis of β,β‐Difluorinated Cyclic Quaternary α‐Amino Acid Derivatives: A Comparative Study

“…It is related to solid-phase synthesis in terms of separation strategies, but rather than employing solid supports, perfluoroalkyl chains are used to facilitate the purification of reaction mixtures. [41] This methodology thus combines the advantages of solid-phase separations and solution-phase reactions in that it facilitates the separation of the synthetic intermediates through fluorous solid-phase ex- traction techniques (F-SPE) [42] while avoiding some of the limitations of solid-phase chemistry, including the unfavorable kinetics, the high amounts of reagents and long reaction times needed, and the difficult analysis of the reaction mixtures through TLC, NMR spectroscopy, or mass spectrometry.…”

Microwave‐Heated Transition Metal‐Catalyzed Coupling Reactions

“…A modern development and variation of solid support is fluorous chemistry [61,62]. Fluorous chemistry is a technique that takes advantage of the unique physical and solubility properties of perfluorinated organic compounds.…”

Fluorous 4‐N,N‐Dimethylaminopyridine (DMAP) Salts as Simple Recyclable Acylation Catalysts

“…[13] Although this strategy originally involved fluorous solvents [14] or silica, [15] the current trend tends toward simple solubility modulation of fluorous catalysts in conventional media, for recovery through precipitation. [16,17] In the field of catalysis, the fluorous approach has been widely applied to metal catalysts by means of fluorinated ligands.…”

“…[16,17] In the field of catalysis, the fluorous approach has been widely applied to metal catalysts by means of fluorinated ligands. [13,14] In contrast, reports on fluorous organocatalysis are still scarce, [18,19] and the field is only at an early stage of development. In this context, we recently reported the preparation of an efficient fluorous aminopyridine for esterification of hindered alcohols, which suffered from poor recyclability.…”