An efficient indium-mediated 2-bromoallylation of aldehydes at low temperature in aqueous DMF

Tetrahedron Letters

Volumn 52, Issue 25, 2011, Pages 3240-3242

  Kim, Yu Mi ^a   Lee, Sangku ^b   Kim, Sung Hwan ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

2 Bromoallylation; Allene; Barbier reaction; Indium

Indexed keywords

2 BROMOHOMOALLYLIC ALCOHOL; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALLENE DERIVATIVE; INDIUM; N,N DIMETHYLFORMAMIDE; REAGENT; UNCLASSIFIED DRUG;

ALLYLATION; AQUEOUS SOLUTION; ARTICLE; BARBIER REACTION; CHEMICAL REACTION KINETICS; DECOMPOSITION; LOW TEMPERATURE;

EID: 79956225330     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.053     Document Type: Article

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39. 11 and our own observations, we assumed that the reaction in aqueous THF at 20 °C could afford the product in a reasonable yield. Actually, the reaction of 1a under the conditions (aqueous THF, 12 h, at 20 °C) gave 62% of 2a. Similarly, the reaction of p-anisaldehyde afforded 2f in 31% (aqueous THF, 14 h, at 20 °C).