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Synthesis of primary propargylic alcohols from terminal alkynes using rongalite as the C1 unit
Miao Wang1, Shan Jiang1, Xin-Xin Lu1
1College of Chemistry and Chemical Engineering, Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang 471022, P. R. China. wangmiao1991@lynu.edu.cn.
Abstract:
Here, an efficient leaving group-activated methylene alcohol strategy for the preparation of primary propargyl alcohols from terminal alkynes by employing the bulk industrial product rongalite as the C1 unit has been described. The reaction avoids the low-temperature reaction conditions and inconvenient lithium reagents required for the classical method of preparing primary propargylic alcohols. Preliminary mechanistic studies showed that the reaction may not proceed via formaldehyde intermediates, but through the direct nucleophilic attack of the terminal alkyne on the carbon atom of rongalite by activation through SO2- as a leaving group.
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