Development and Application of a Multielectron-Accepting Organic Oxidant for the Catalytic Transition-Metal-Free Oxidative Homocoupling of Grignard Reagents in Air

Research paper by Toshinobu Korenaga, Kaoru Nitatori, Hiroki Muraoka, Satoshi Ogawa, Kazuaki Shimada

Indexed on: 28 Oct '15Published on: 27 Oct '15Published in: Organic Letters


Heptafluorotolyl-substituted perfluorocyclopentene acts as a four-electron oxidant for the homocoupling of Grignard reagents. It can also be used for catalytic homocoupling with a low catalyst loading (up to 2 mol %) in the presence of atmospheric oxygen. The organocatalytic cycle involves the generation of an organic radical and a perfluorocyclopentadienyl anion.

Graphical abstract orglet.10.jpg