FLP chemistry continues to afford remarkable reactions that proceed without transition metals. Metal-free aromatic hydrogenation of N -bound phenyl rings can be achieved in the presence of H2 and B(C6F5)3 to form N - cyclohexylammonium hydridoborate salts (T. Mahdi, Z. M. Heiden, S. Grimme, D. W. Stephan, J. Am. Chem. Soc. , 2012 , 134 , 4088).
a. Sketch the reaction coordinate diagram in Figure 2 of this report, including the structures of intermediates and transition states.
b. Discuss the hypothesized steps for initial addition of H+ to the aromatic ring of t–BuNHPh .
c. How does this diagram support the outcome of the reaction of t–BuNHPh , B(C6F5)3 , and H2 in pentane (at 298 K) versus in refluxing toluene (383 K)?
d. What happens if the utilized amine becomes too basic?
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