Tin-Indium Mediated and Microwave Assisted Propargylation of Aldehydes with Propargyl Bromide
Qian-Rong Li
Project supported by the Natural Science Foundation of Anhui Province (No. 03045305).
Search for more papers by this authorCheng-Zhi Gu
Structure Research Laboratory, University of Science and Technology of China, Hefei, Anhui 230026, China
Department of Chemistry, Shihezi Univeristry, Shihezi, Xinjiang 832003, China
Search for more papers by this authorHao Yin
Structure Research Laboratory, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorQian-Rong Li
Project supported by the Natural Science Foundation of Anhui Province (No. 03045305).
Search for more papers by this authorCheng-Zhi Gu
Structure Research Laboratory, University of Science and Technology of China, Hefei, Anhui 230026, China
Department of Chemistry, Shihezi Univeristry, Shihezi, Xinjiang 832003, China
Search for more papers by this authorHao Yin
Structure Research Laboratory, University of Science and Technology of China, Hefei, Anhui 230026, China
Search for more papers by this authorAbstract
A rapid and regioselective preparation of homopropargyl alcohols was reported. In the presence of SnCl2-C6H5Me3NBr and microwave irradiation, the mixture of tin-indium and propargyl bromide reacted quickly with aldehydes in aqueous media to produce the homopropargyl alcohols exclusively in high yields. For benzaldehydes bearing different substituents, electronic effect of the substituents affected the reaction, the electron-withdrawing groups promoting the reaction and the electron-donating groups impeding the reaction. The reactions of benzaldehydes bearing an orthosubstituent group on the phenyl ring with propargyl bromide may yield a mixture of regioisomers (homopropargyl and homoallenyl alcohols) or a single homoallenic alcohol due to the steric effect.
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