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The mechanism of organotrifluoroborate-based Suzuki-Miyaura coupling reactions has recently been investigated in detail. The organotrifluoroborate hydrolyses to the corresponding boronic acid in situ , so a boronic acid can be used in place of an organotrifluoroborate, as long as it is added slowly and carefully.
The Suzuki reaction or Suzuki coupling is an organic reaction that uses a palladium complex catalyst to cross-couple a boronic acid to an organohalide. [1] [2] [3] It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of noble metal catalysis in organic ...
Variations include another CF 3 donor potassium (trifluoromethyl)trimethoxyborate, [38] the use of aryl boronic acids [39] [40] or the use of a trifluoromethyl sulfonium salt [41] or the use of a trifluoromethylcopper(I) phenanthroline complex. [42]
Organoboron. Organoboron chemistry or organoborane chemistry studies organoboron compounds, also called organoboranes.These chemical compounds combine boron and carbon; typically, they are organic derivatives of borane (BH 3), as in the trialkyl boranes.
A triflate group is an excellent leaving group used in certain organic reactions such as nucleophilic substitution, Suzuki couplings and Heck reactions.Since alkyl triflates are extremely reactive in S N 2 reactions, they must be stored in conditions free of nucleophiles (such as water).
Potassium fluoroborate is obtained by treating potassium carbonate with boric acid and hydrofluoric acid. B(OH) 3 + 4 HF → HBF 4 + 3 H 2 O 2 HBF 4 + K 2 CO 3 → 2 KBF 4 + H 2 CO 3. Fluoroborates of alkali metals and ammonium ions crystallize as water-soluble hydrates with the exception of potassium, rubidium, and cesium.
4-Formylphenyl boronic acid crystallizes in colorless needles [2] or is obtained as an odorless, whitish powder, which dissolves little in cold but better in hot water. The compound is quite stable [4] and readily forms dimers and cyclic trimeric anhydrides, which complicate purification and tend to protodeboronize, a secondary reaction that occurs frequently in the Suzuki coupling, with ...
Potassium tris(3,5-dimethyl-1-pyrazolyl)borate, abbreviated KTp*, is the potassium salt of the anion HB((CH 3) 2 C 3 N 2 H) 3. Tp* − is a tripodal ligand that binds to a metal in a facial manner, more specifically a Scorpionate ligand. [1] KTp* is a white crystalline solid that is soluble in polar solvents, including water and several alcohols.