Substituent effects on aryltrifluoroborate solvolysis in water: implications for Suzuki-Miyaura coupling and the design of stable (18)F-labeled aryltrifluoroborates for use in PET imaging.
J Org Chem
; 73(12): 4662-70, 2008 Jun 20.
Article
em En
| MEDLINE
| ID: mdl-18489162
ABSTRACT
Whereas electron withdrawing substituents retard the rate of aryltrifluoroborate solvolysis, electron-donating groups enhance it. Herein is presented a Hammett analysis of the solvolytic lability of aryltrifluoroborates where log(k(solv)) values correlate to sigma values with a rho value of approximately -1. This work provides a predictable rubric for tuning the reactivity of boron for several uses including (18)F-labeled PET reagents and has mechanistic implications for ArBF(3)-enhanced ligandless metal-mediated cross coupling reactions with aryltrifluoroborates.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos de Boro
/
Água
/
Tomografia por Emissão de Pósitrons
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article