Transitioning Organic Synthesis from Organic Solvents to Water: Following Nature's Lead

April 1, 2016

Bruce Lipshutz

Three  key  reaction  variables  important  to  synthetic  chemists  include  the  reaction  solvent,  reaction  temperature,  and  the  choice  of  catalyst.  The  medium  in  which  organic  synthesis  is performed is usually organic, while most reactions tend to require either heating or cooling. The catalyst typically involves a metal, and more often than not, is a precious metal such as palladium. This  presentation  will  offer  a  win-­‐win-­‐win  situation,  addressing  all  of  these  issues  from  the  standpoint of both economics and the environment. Several valued reactions in organic synthesis will be discussed that can be run in water, with most taking place at room temperature. Equally importantly, given that Pd is both costly and an endangered metal, these can now be effected using ppm levels of palladium, made possible by development of a new ligand, “HandaPhos”, enabled by its  use  in  aqueous  nanomicelles  composed  of  a  designer  surfactant  (e.g.,  TPGS-­‐750-­‐M  or  Nok).  Unpublished  work  will  focus  on  this  new  Pd  chemistry,  and  will  then  shift  to  a  complementary technology that involves new Fe-­‐based nanoparticles applied to such cross-­‐couplings and related reactions of considerable interest, especially to the pharmaceutical industry.