A Facile Preparation of Hydroxylated Potassium Organotrifluoroborates and Their Jones Oxidation to Potassium Organocarbonyltrifluoroborates
- A Facile Preparation of Hydroxylated Potassium Organotrifluoroborates and Their Jones Oxidation to Potassium Organocarbonyltrifluoroborates
- 함정엽; 볼라 크리쉬나베뉴; 김동수; 송중호; 이혜진; 박순혜
- Jones Oxidation; Hydroxylated Organotrifluoroborates; Organocarbonyltrifluoroborates
- Issue Date
- Twelfth Tetrahedron Symposium
- Organotrifluoroborate salts have been recognized as useful synthetic reagents in the Suzuki-Miyaura cross-coupling reaction. Recently, methods for the direct functionalization of
organotrifluoroborates, using their property of inertness under various reaction conditions, has been developed and used for the preparation of more complex organotrifluoroborates,
which may be difficult to prepare by conventional syntheses of organoboron reagents. As part of the study to prepare functionalized potassium organotrifluoroborates for use as new
coupling reagents in the Suzuki-Miyaura cross-coupling reaction, we discovered that potassium organocarbonyltrifluoroborates are readily obtained from the treatment of primary or
secondary alcohol-containing organotrifluoroborates with Jones reagent. The Jones oxidation is generally performed in acetone as a solvent in which potassium organotrifluoroborate
salts are soluble. Thus, potassium counterion salts can be used immediately without the need for converting them into TBA salts. Also, we confirmed that these hydroxylated potassium
organotrifluoroborates can tolerate under Jones oxidation conditions contrary to other organoboron derivatives. In this presentation, we report a facile one-pot synthesis of secondary
alcohol-containing organotrifluoroborates from their corresponding dibromobenzenes, followed by the convenient preparation of potassium organocarbonyltrifluoroborates via Jones
oxidation and the cross-coupling reactions of these organocarbonyltrifluoroborates in the presence of 3 mol % Pd(PPh3)4 catalyst at 100 ℃.
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