cheminform abstract: one-pot preparation of hydroxylated potassium organotrifluoroborates and...

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ChemInform 2011, 42, issue 01 © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Organo-boron compounds S 0040 DOI: 10.1002/chin.201124176 One-Pot Preparation of Hydroxylated Potassium Organotrifluoroborates and Subsequent Jones Oxidation to Potassium Organocarbonyltrifluoroborates. Dibromobenzenes (I) or (VII) and a range of aromatic and aliphatic aldehydes are se- quentially transformed into alcohol-containing organotrifluoroborates via lithi- um—halogen exchange reactions. A quenching of the following Jones oxidation reac- tion by K 2 CO3 is necessary to prevent a decomposition of the formed ketones by resid- ual sulfuric acid. In addition, under optimized conditions Suzuki—Miyaura cross-cou- pling reactions are performed with the organocarbonyltrifluoroborates. — (KIM, D.-S.; BOLLA, K.; LEE, S.; HAM*, J.; Tetrahedron 67 (2011) 6, 1062-1070, http://dx.doi.org/10.1016/j.tet.2010.12.049 ; Nat. Prod. Res. Cent., Korea Inst. Sci. Technol., Gangwon, Gangneung 210-340, S. Korea; Eng.) — Klein 24- 176

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Organo-boron compoundsS 0040 DOI: 10.1002/chin.201124176

One-Pot Preparation of Hydroxylated Potassium Organotrifluoroborates and Subsequent Jones Oxidation to Potassium Organocarbonyltrifluoroborates. — Dibromobenzenes (I) or (VII) and a range of aromatic and aliphatic aldehydes are se-quentially transformed into alcohol-containing organotrifluoroborates via lithi-um—halogen exchange reactions. A quenching of the following Jones oxidation reac-tion by K2CO3 is necessary to prevent a decomposition of the formed ketones by resid-ual sulfuric acid. In addition, under optimized conditions Suzuki—Miyaura cross-cou-pling reactions are performed with the organocarbonyltrifluoroborates. — (KIM, D.-S.; BOLLA, K.; LEE, S.; HAM*, J.; Tetrahedron 67 (2011) 6, 1062-1070, http://dx.doi.org/10.1016/j.tet.2010.12.049 ; Nat. Prod. Res. Cent., Korea Inst. Sci. Technol., Gangwon, Gangneung 210-340, S. Korea; Eng.) — Klein

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ChemInform 2011, 42, issue 01 © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim