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: The Ohio State University
EPA Project Officer: Hahn, Intaek
Project Period: October 1, 1995 through September 30, 1997
Project Amount: $300,000
RFA: Technology for a Sustainable Environment (1995) Recipients Lists
Research Category: Sustainability , Pollution Prevention/Sustainable Development


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 11 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., RFA, Scientific Discipline, Sustainable Industry/Business, Chemical Engineering, cleaner production/pollution prevention, Environmental Chemistry, Sustainable Environment, Technology for Sustainable Environment, Economics and Business, aldehydes, cleaner production, indium-promoted carbon bond forming, waste minimization, waste reduction, environmentally benign solvents, carbon bond formation, carbon-carbon binding, alternative materials, allylic halides, innovative technology, hydroxyl radicals, pollution prevention, source reduction, catalysis, green chemistry

Progress and Final Reports:

  • 1996
  • Final Report