Indium-Mediated Synthesis of Homoallyl Alcohols in the Aqueous Phase

Abstract

The indium-mediated Barbier-type allylation reaction of aldehydes with allyl bromide, which gives corresponding homoallyl alcohols, was investigated. The reaction medium and the effects of substituents were discussed in detail. The results showed that various aldehydes, including aromatic, heterocyclic, and aliphatic aldehydes, with different substituents could all react well with excellent yields of 91–97% in aqueous tetrahydrofuran at room temperature within about 1 h.

Keywords:

• Aldehydes
• allylation reaction
• aqueous reaction
• homoallyl alcohols
• indium

ACKNOWLEDGMENTS

We gratefully acknowledge Natural Science Foundation of China (20702042), Key Laboratory of Polymer Materials of Gansu Province (zd-06-18), and NWNU Young Teachers Research Improving Program (NWNU-LKQN-10-11) for financial support.

Notes

^a Reaction conditions: 2-methoxy benzaldehyde (1 mmol), allyl bromide (1.5 mmol), rt, TLC detection.

^b Isolated yield after column chromatography.

^a Reactions conditions: indium (1 mmol), aldehyde (1 mmol), allyl bromide (1.5 mmol), THF (2 mL), water (0.5 mL), rt TLC tracked.

^b Isolated yield after column chromatography; all the products were characterized thoroughly by ¹H and ¹³C NMR.

^c The reaction was conducted in 40 °C water bath.