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Opportunities Offered by Indium-Promoted Carbon-Carbon Bond-Forming Reactions in Water

EPA Grant Number: R824725
Title: Opportunities Offered by Indium-Promoted Carbon-Carbon Bond-Forming Reactions in Water
Investigators: Paquette, Leo A.
Institution: Ohio State University - Main Campus
EPA Project Officer: Karn, Barbara
Project Period: October 1, 1995 through September 30, 1997
Project Amount: $300,000
RFA: Technology for a Sustainable Environment (1995)
Research Category: Pollution Prevention/Sustainable Development

Description:

This research project seeks to generalize on the serviceability of free hydroxyl groups for promoting stereochemical control in organic reactions performed in aqueous environments under catalysis by indium metal. Emphasis is initially being placed on establishing those structural features within carbonyl compounds most conducive to achieving high levels of stereoselectivity. An exemplary thrust involves enforced axial and equatorial orientation of the hydroxyl substituent at alpha- and beta-sites in order to determine their impact on stereoinduction. To be investigated subsequently, will be a wide range of diastereoselective reactions where installation of three or more contiguous stereogenic centers operate. While the initial phases of this investigation shall involve allylic halides for simplicity and convenience, the workability of various other types of potentially reactive halides is also to be probed. It is already clear that tremendous advantages can accrue from the use of the indium-water catalyst system. For example, protection/deprotection steps are no longer necessary. In addition, atom economy is served in an outstanding fashion and reactions proceed at significantly enhanced rates. Should enantioselective addition reactions operate at high levels of chiral induction under these conditions (with added chiral promoter), the project will expand to encompass the full evaluation of these processes as well.

Publications and Presentations:

Publications have been submitted on this project: View all 13 publications for this project

Journal Articles:

Journal Articles have been submitted on this project: View all 13 journal articles for this project

Supplemental Keywords:

Green chemistry, carbon-carbon bonding, aqueous and organic solvents, diastereoselection, 1,2 allylindium reagents, thia and a-amino aldehydes in indium-promoted coupling, allelic bromides. , Sustainable Industry/Business, Scientific Discipline, RFA, Technology for Sustainable Environment, Sustainable Environment, Chemical Engineering, cleaner production/pollution prevention, Environmental Chemistry, Economics and Business, aqueous solvents, cleaner production, waste reduction, carbon-carbon binding, green chemistry, carbon bond formation, allylic halides, waste minimization, hydroxyl radicals, environmentally benign solvents, alternative materials, indium-promoted carbon bond forming, source reduction, catalysis, aldehydes, innovative technology

Progress and Final Reports:
Final Report

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The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Conclusions drawn by the principal investigators have not been reviewed by the Agency.

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