From Minutes to Years: Predicting Organotrifluoroborate Solvolysis Rates. Issue 10 (30th January 2015)

• Record Type: Journal Article
• Authors: Liu, Zhibo; Chao, Daniel; Li, Ying; Ting, Richard; Oh, Jihyoon; Perrin, David M.
• Is Part Of: Chemistry. Volume 21:Issue 10(2015)
• Page Start: 3924
• Page End: 3928
• Publication Date: 2015-01-30
• Subjects: organotrifluoroborates -- positron emission tomography -- solvolysis -- Suzuki–Miyaura cross coupling; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201405829
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Organotrifluoroborates solvolyze in water at rates that vary over five orders of magnitude. The negative logarithm of the solvolytic rate constant, p k (BF), correlates exceptionally well with the p K a of the analogous carboxylic acid ( R 2 =0.984). This unforeseen correlation may be of predictive value for several applications including Suzuki–Miyaura cross‐coupling reactions and the design of 18 F‐organotrifluoroborate radioprosthetic groups. Abstract : Like BF3 alling off a log : Organotrifluoroborates solvolyze in water at rates that vary over five orders of magnitude. The negative logarithm of the solvolytic rate constant, p k (BF), correlates exceptionally well with the p K a of the analogous carboxylic acid (see figure). This unforeseen correlation may be of predictive value for several applications including Suzuki–Miyaura cross‐coupling reactions and the design of 18 F‐organotrifluoroborate radioprosthetic groups.