Selective reductions and reductive aminations with ammonia-borane

ORGN 95

Alysia A. Lowe1, P. Veeraraghavan Ramachandran1, and Paul Clark2. (1) Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, (2) Advanced Power Systems, General Atomics, 3483 Dunhill St., San Diego, CA 92121
Ammonia-borane (AB) is actively pursued as a potential hydrogen storage material for fuel-cell applications. There are very few reports on the organic chemistry applications of this reagent. This could be partly due to the high cost of this chemical. As part of our program on “hydrogen energy”, we have developed a simple and large-scale preparation of ammonia borane in high yields and purity. This allowed the examination of ammonia-borane for large-scale organic chemistry applications. We have examined AB for the selective reduction of representative classes of organic molecules. We have discovered that AB can be utilized for the selective reduction of ketones and aldehydes in water or alcohol as solvent medium. Reudctive amination of amines and carbonyls were also achieved readily in the presence of ammonia borane. Details of our systematic examination of AB for the reduction of representative examples of several functional groups and the successful reduction of aldehydes and ketones and reductive aminations will be presented.
 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008