Alkynylation of aldehydes mediated by zinc and allyl bromide: a practical synthesis of propargylic alcohols

• DOI: 10.1007/s11164-016-2859-2
• Publication Date: 2017-02-07T09:19:22Z
• Authors: Ji-Cai Zhou; Lei Zhao; Yuan Li; Ding-Qiang Fu; Zi-Cheng Li; Wen-Cai Huang
• Keywords: 01 natural sciences; 0104 chemical sciences

A practical synthesis of propargylic alcohols was developed by alkynylation of aldehydes mediated by zinc and allyl bromide. Aromatic, aliphatic and vinyl aldehydes react with phenylacetylene or 1-hexyne to obtain various propargylic alcohols at room temperature in up to 98% yield. This method is characterized with inexpensive materials, wide substrate scope, and mild reaction conditions, and is also easy to scale up. In addition, this protocol is applicable to the alkynylation of α-ketone esters and epoxides to generate α-tertiary-hydroxy esters and α-alkynyl alcohols, respectively.