Distiboranes based on ortho-phenylene backbones as bidentate Lewis acids for fluoride anion chelation.
Org Biomol Chem
; 19(22): 4949-4957, 2021 06 09.
Article
em En
| MEDLINE
| ID: mdl-33988214
ABSTRACT
As part of our efforts in the chemistry of main group platforms that support anion sensing and transport, we are now reporting the synthesis of anitmony-based bidentate Lewis acids featuring the o-C6F4 backbone. These compounds can be easily accessed by reaction of the newly synthesized o-C6F4(SbPh2)2 (5) with o-chloranil or octafluorophenanthra-9,10-quinone, affording the corresponding distiboranes 6 and 7 of general formula o-C6F4(SbPh2(diolate))2 with diolate = tetrachlorocatecholate for 6 and octafluorophenanthrene-9,10-diolate for 7, respectively. While 6 is very poorly soluble, its octafluorophenanthrene-9,10-diolate analog 7 readily dissolves in CH2Cl2 and undergoes swift conversion into the corresponding fluoride chelate complex [7-µ2-F]- which has been isolated as a [nBu4N]+ salt. The o-C6H4 analog of 7, referred to as 8, has also been prepared. Although less Lewis acidic than 7, 8 also forms a very stable fluoride chelate complex ([8-µ2-F]-). Altogether, our experiental results, coupled with computational analyses and fluoride anion affinity calculations, show that 7 and 8 are some of the strongest antimony-based fluoride anion chelators prepared to date. Another notable aspect of this work concerns the use of the octafluorophenanthrene-9,10-diolate ligand and its ablity to impart advantageous solubility and Lewis acidity properties.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2021
Tipo de documento:
Article
País de afiliação:
Estados Unidos