Work

1,2-Halogen Migration in Haloallenyl Ketones: Regiodivergent Synthesis of Halofurans

Year: 2005

Type: article

Abstract: Selective 1,2-iodine, bromine, and chlorine migration in haloallenyl ketones in the presence of Au catalyst has been demonstrated. It was found that, depending on the nature of the Au catalyst used, either selective bromine migration or hydrogen shift occurs, leading to the formation of 3- or 2-bromofurans, respectively. Halirenium intermediate was proposed for the unusual 1,2-halogen migration. This cascade transformation allows for mild and efficient synthesis of various types of 3-halofurans.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja053290y

Authors: Anna W. Sromek, Marina Rubina, Vladimir Gevorgyan

Institution: University of Illinois Chicago

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1142569753, Novel Direct Approaches Toward Bioactive Heterocycles