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Palladium(O) and rhodium(I) catalysis of the carbonylation of unactivated bromides

✍ Scribed by Khaled E. Hashem; James B. Woell; Howard Alper

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 119 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)91248-1

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✦ Synopsis

Alkyl vinyl and aromatic bromides react with organoborates and carbon monoxide, in asence of Catalytic quantities of 1,5-hexadienerhodium(1) chloride dimer and tetrakis(triphenylphosphine)palladium(O),to give carboxylic esters in good yields. Recently, we reported the first examples of metal catalysis of a borate ester reaction. Benzylic bromides react with borate esters and carbon monoxide, in the presence of 1,5-hexadienerhodium(1) chloride dimer[l,S-HDRhCl]B, to give esters in excellent yields. Unfortunately, no reaction occurred with less activated bromides, such as 1-bromonaphthalene or I-bromooctane. This lack of reactivity might be due to the possibility that complex 2, obtained by reaction of 3ArCH2Br + B(OR')3 + 3C0 [1,5-HDRhC112

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