Facile one-pot reaction for the synthesis of ketones from acid chlorides and organo lithium in the presence of MgI2

ORGN 156

Han-Xun Wei, hwei@rics.bwh.harvard.edu1, Vivien Sun2, Peter M. Young2, and Corinne E. Augelli-Szafran2. (1) Center for Neurological Diseases, Harvard Medical School and Brigham and Women's Hospital, 77 Avenue Louis Pasteur, Boston, MA o2115, (2) Center for Neurological Diseases, Harvard Medical School and Brigham and Women’s Hospital
The reaction of acid chlorides with organolithium reagents usually does not give aryl ketones in high yields. This perhaps may be due to the high reactivity of the intermediate ketones with the organometallic reagent. However, in our laboratories, we have recently found that in the presence of MgI2, organolithium behaves like n-butyl lithium can easily react with various acid chlorides to give the desired ketones in high yield. This one pot reaction has advantages over other ketone syntheses that involve more than one step, such as the Weinreb ketone synthesis. Various examples and the utility of this new methodology 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