^tBuOLi-Mediated Alkynylation of Aldehydes

Abstract

The lithium tert-butoxide reagent was found to promote the addition of terminal aromatic alkynes to various aromatic aldehydes. This reaction was efficiently carried out in anhydrous dimethylformamide at room temperature in air for 50 min, and the corresponding propargylic alcohols were obtained in good to excellent yields (up to 95%).

Keywords:

• Alkynylation
• lithium tert-butoxide
• propargylic alcohol

ACKNOWLEDGMENTS

The authors are grateful to the project sponsored by the Scientific Research Foundation for the State Education Ministry (No. 107108) and the National Natural Science Foundation of China (No. J0730425).

Notes

^a All reactions were carried out in anhydrous solvent at room temperature in air for 50 min.

^b Isolated yields based on the benzaldehyde.

^c ND, not detected.

^d Commercial DMF.

^a All reactions were carried out using 1.0 equiv of benzaldehyde, 2.0 equiv of ^tBuOLi, 1.2 equiv of phenylacetylene, and 1.5 ml of DMF at room temperature for 50 min.

^b Isolated yield based on the aldehyde.

^c ND, not detected.