Ether: the new hydrogenation reagent

27 July 2013 - Miracles

We are teasing of course. Nevertheless it continues to amaze that even in 2013 you can throw a selection of regular household chemicals together and discover completely new chemistry. Take Lindsay J. Hounjet et al. here (Stephan and Grimme accounted for) who in a brainwave combined Tris(pentafluorophenyl)boron, diethylether and hydrogen gas. Well, not exactly hydrogen gas but HD gas which allowed them to ascertain (by NMR experiment) that hydrogen exchange was taking place. And if you say hydrogen exchange you say hydrogenation. And yes, the combination of B(C6F5)3, Et2O, CD2Cl2 and H2 and anthracene results in hydrogenation. The key frustrated Lewis pair in play here is (Et2O)2H+ H(B(C6F5)3)-. Humble ether ripping apart dihydrogen with a little help from a friend.

I dare you: take the Sigma-Aldrich catalogue, select any combination of chemicals on stock and discover new chemistry worthy of publication from a single reaction. Difficult? Lindsay J. Hounjet thinks not.