Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters

Katie M J Feeney, Guillaume Berionni, Herbert Mayr*, Varinder K. Aggarwal

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

22 Citations (Scopus)

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 languageEnglish
Pages (from-to)2614-2617
Number of pages4
JournalOrganic Letters
Volume17
Issue number11
DOIs
Publication statusPublished - 5 Jun 2015

Structured keywords

  • BCS and TECS CDTs

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