Structure and Reactivity of Boron-Ate Complexes Derived from Primary and Secondary Boronic Esters

Org. Lett., 2015, 17, 2614-2617

Org. Lett.

Boron-ate complexes derived from primary and secondary boronic esters and aryllithiums have been isolated, and the kinetics of their reactions with carbenium ions studied. The second-order rate constants have been used to derive nucleophilicity parameters for the boron-ate complexes, revealing that nucleophilicity increased with (i) electron-donating aromatics on boron, (ii) neopentyl glycol over pinacol boronic esters, and (iii) 12-crown-4 ether.

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