Stephan et al. have reported metal-free hydrogenation of
N-substituted aniline using H
2 and
B(C6F5)3.
1) Sterically encumbered Lewis acid (
B(C6F5)3) and Lewis base (
N-substituted aniline) are combined to form the unquenched “frustrated Lewis pairs (FLPs)
2)” which is available to carry out unusual reactions. In this reaction, the boron mediates uptake of H
2, terminating with a final FLP activation of H
2 to enable the hydrogenation to proceed under metal free conditions.