Abstract
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.
Original language | English |
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Pages (from-to) | 2614-2617 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 17 |
Issue number | 11 |
DOIs | |
Publication status | Published - 5 Jun 2015 |
Externally published | Yes |