Transition-metal hydrides phenol

Most of the alkyls of the other early transition metals demonstrate similar reactivity.101102 Hydridic metal hydrides will similarly react with the weakly acidic OH groups of alcohols and phenols, liberating hydrogen and forming alkoxides or phenoxides. Aluminum hydride will undergo stepwise substitution by alcohols (equation 29).103... 

From the point of view of catalytic strategy, all three of these facts are probably connected. The product of the reaction is a phenol, rather than an enolate, and metal ion stabilization of the product is apparently not needed. The driving force associated with formation of an aromatic compound is evidently sufficient that decarboxylation can be concerted with hydride transfer. The carbon isotope effect on this reaction is surprisingly small, perhaps because the transition state is quite early (65). The isotope effects also indicate that substrate binding is associated with a conformation change, which may seat the substrate in a reactive conformation in the active site. 

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