A general and mild copper-catalyzed arylation of diethyl malonate

Organic Letters

Volumn 4, Issue 2, 2002, Pages 269-272

  Hennessy, Edward J ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; COPPER; DIETHYLMALONIC ACID; IODINATED HYDROCARBON; MALONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; COPPER; HYDROCARBONS, AROMATIC; HYDROCARBONS, IODINATED; MALONATES;

EID: 0037165422     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017038g     Document Type: Article

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46. We found that the yields were slightly higher in entries 13 and 15 when 3 equiv of malonate was used to suppress competing processes, presumably carbon-heteroatom bond formation.
47. The use of bromobenzene in place of iodobenzene afforded only trace amounts (<2%) of the α-aryl malonate.
48. Even in these cases, though, there is usually less than 10% decarboxylation.
49. In the absence of 2-phenylphenol, the arylation of iodobenzene under the aforementioned reaction conditions proceeded to only ∼80% conversion.
50. 4), filtered through a plug of Celite, and concentrated on a rotary evaporator. The material thus obtained was purified by silica gel chromatography to give the product α-aryl malonate.