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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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From minutes to years: predicting organotrifluoroborate solvolysis rates
Zhibo Liu1, Daniel Chao, Ying Li
1Chemistry Department, 2036 Main Mall, University of British Columbia, Vancouver, BC, V6T 1Z1 (Canada).
Abstract:
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 (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.
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