A Facile Preparation of Hydroxylated Potassium Organotrifluoroborates and Their Jones Oxidation to Potassium Organocarbonyltrifluoroborates

Title
A Facile Preparation of Hydroxylated Potassium Organotrifluoroborates and Their Jones Oxidation to Potassium Organocarbonyltrifluoroborates
Authors
함정엽볼라 크리쉬나베뉴김동수송중호이혜진박순혜
Keywords
Jones Oxidation; Hydroxylated Organotrifluoroborates; Organocarbonyltrifluoroborates
Issue Date
2011-06
Publisher
Twelfth Tetrahedron Symposium
Abstract
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 ℃.
URI
http://pubs.kist.re.kr/handle/201004/39993
Appears in Collections:
KIST Publication > Conference Paper
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