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Tin‐Indium Mediated and Microwave Assisted Propargylation of Aldehydes with Propargyl Bromide
Author(s) -
Li QianRong,
Gu ChengZhi,
Yin Hao
Publication year - 2006
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200690024
Subject(s) - chemistry , propargyl bromide , substituent , bromide , propargyl , regioselectivity , propargyl alcohol , tin , indium , steric effects , yield (engineering) , alcohol , organic chemistry , medicinal chemistry , catalysis , materials science , metallurgy
A rapid and regioselective preparation of homopropargyl alcohols was reported. In the presence of SnCl 2 ‐C 6 H 5 Me 3 NBr 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 ortho substituent 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.