Facile Preparation of Fluorine-containing Alkenes, Amides and Alcohols via the Electrophilic Fluorination of Alkenyl Boronic Acids and Trifluoroborates

Synthetic Methods for Fluorinated Olefins

“…Petasis, Prakash, and Olah, for example, reported reactions of alkenyl trifluoroborates with Selectfluor TM (Scheme 20). [40] With the use of an equimolar amount of Selectfluor TM , the alkenyl trifluoroborates 19 could be converted into the corresponding fluoro-olefin Alkenylsilanes and alkenylstannanes showed similar reactivities in reactions with Selectfluor TM (Scheme 21). Gouverneur reported that an E/Z mixture of fluoro-olefins was obtained in moderate yield from the fluorination reaction of the (E)-alkenyltrimethylsilane 22 with Selectfluor TM (1.0 equiv.)…”

Synthesis of enantiopure 2‐(aminoalkyl)phenol derivatives and their application as catalysts in stereoselective reactions

“…[42][43][44][45][46][47][48][49] It is interesting that the synthesis of variously functionalized 2-(aminoalkyl)phenols through the condensation of alkenyl, aryl, or heteroaryl boronic acids with amines and salicylaldehydes. 50 The final 2-(aminoalkyl)-phenol 12 is obtained through an intramolecular addition (Scheme 7).…”

Potassium Organotrifluoroborates: New Partners in Palladium-Catalysed Cross-Coupling Reactions

“…Until now, the only utility of potassium organotrifluoroborates has been their ability to release organodifluoroboranes upon heating [16a] or treatment with chlorotrimethylsilane, [12] [18] although very recently they have been used in the preparation of fluoroalkenes. [19] Scheme 3. In situ formation of potassium aryltrifluoroborates from As described previously, [12] treatment of commercial aryl-aryl bromides boronic acids with aqueous KHF 2 resulted in the instantaneous deposition of a voluminous precipitate of the poIn the same way, treatment of the readily available alkentassium aryltrifluoroborate.…”

“…This gave an indication observed, arising mainly from reduction (4 and 5) and of the substitution at the boron atom. In the 19 F-NMR homocoupling (6 and 7) of these substrates. spectra, 1:1:1:1 quadruplets were observed, as expected for…”

“…We first studied the influence of the solvent on the course the coupling of 19 F with 11 B of spin 3/2. In the 13 C-NMR of the reaction using palladium acetate as catalyst (Table 2, entries 1Ϫ9).…”