Details

Autor(en) / Beteiligte

• Liu, Zhibo
• Chao, Daniel
• Li, Ying
• Ting, Richard
• Oh, Jihyoon
• Perrin, David M.

Titel

From Minutes to Years: Predicting Organotrifluoroborate Solvolysis Rates

Ist Teil von

• Chemistry : a European journal, 2015-03, Vol.21 (10), p.3924-3928

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2015

Quelle

Wiley InterScience Journals

Beschreibungen/Notizen

• Organotrifluoroborates solvolyze in water at rates that vary over five orders of magnitude. The negative logarithm of the solvolytic rate constant, pk(BF), correlates exceptionally well with the pKa of the analogous carboxylic acid (R2=0.984). This unforeseen correlation may be of predictive value for several applications including Suzuki–Miyaura cross‐coupling reactions and the design of 18F‐organotrifluoroborate radioprosthetic groups. Like BF3alling off a log: Organotrifluoroborates solvolyze in water at rates that vary over five orders of magnitude. The negative logarithm of the solvolytic rate constant, pk(BF), correlates exceptionally well with the pKa 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 18F‐organotrifluoroborate radioprosthetic groups.