A useful base applied in the Suzuki carbonylative coupling of enol triflates with vinyl boronic acids,1 and in Knoevenagel condensation reactions to give higher yields than KF or NaF.2 Less hygroscopic alternative to tetra-n-butylammonium fluoride (TBAF) and TAS-fluoride (TASF) when anhydrous "naked" fluoride ion is needed. A popular source of fluoride used in conversion of electron-deficient aryl chlorides to aryl fluorides.3 Useful for desilylation reactions 2 and for the removal of silyl protecting groups.4 Employed in the successful synthesis of a single-crystal Dion-Jacobson phase, CsLaTa2O7, that has applications in photocatalysis and superconductivity.5 As a catalyst in the synthesis of flavones and their derivatives from esters of 2-hydroxyacetophenones and in the synthesis of tobacco alkaloids from aromatic amides,6 and in the addition of trimethylsilylcyanide to ketones.7 Used in synthesis of macrocyclic polyethers with aromatic subunits.8 Also applied to promote halogenation of cyanogen by chlorine and bromine,9 and promote Stille coupling reaction.10
References
1. Eur. J. Org. Chem. 2007, 2152.
2. Tetrahedron Lett. 1985, 26, 787.
3. J. Org. Chem. 1968, 33,1837.
4. Org. Synth. 2002, 78, 82.
5. Chem. Abstr. 1998, 129, 224819u.
6. React.Kinet.Catal.Lett. 2001, 72, 3.
7. J. Org. Chem. 2004, 689, 1734.
8. J. Heterocycl. Chem. 1985, 22, 1297.
9. Inorg. Chem. 1991, 30, 535.
10. Chem. Commun. 2008, 6330.