Palladium(II)-catalyzed synthesis of 2-alkoxytetrahydrofurans from allylic alcohols and vinyl ethers: Stereospecificity and catalysis
Palladium(II)-catalyzed synthesis of 2-alkoxytetrahydrofurans from allylic alcohols and vinyl ethers: Stereospecificity and catalysis
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DOI：
10.1055/s-2006-951513
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发表时间：
2006-11-03
期刊：
影响因子：
2
通讯作者：
Hosokawa, Takahiro
中科院分区：
文献类型：
--
作者：
Kawamura, Yasufumi;Imai, Takuro;Hosokawa, Takahiro
在Pd（Ac）（2）、Cu（Ac）（2）和邻苯二酚（1：1：2）组成的催化剂作用下，（E）-或（Z）-肉桂醇与乙烯基乙醚在氧气气氛下反应，分别得到了（Z）-或（E）-4-亚苄基-2-乙氧基四氢呋喃的高产率。类似地，由烯丙醇和丁基乙烯基醚得到2-丁氧基-4-外亚甲基四氢呋喃。然而，在烯丙醇的情况下，即使在较低的钯/底物比，例如催化剂浓度为1摩尔%的情况下，如果使用相对大量的Pd（0Ac）（2），例如0.25 - 0.05毫摩尔，则催化不能很好地进行以形成钯黑。
The reaction of (E)- or (Z)-cinnamyl alcohol and ethyl vinyl ether with a catalyst consisting of Pd(OAc)(2), Cu(OAc)(2), and catechol (1:1:2) under 02 gives a good yield of (Z)- or (E)-4-benzylidene-2-ethoxytetrahydrofuran, respectively. Similarly, 2-butoxy-4-exomethylenetetrahydrofuran was obtained from allyl alcohol and butyl vinyl ether. In the case of allyl alcohol, however, the catalysis does not proceed well with forming palladium black, if a relatively large amount of Pd(OAc)(2), such as 0.25 mmol to 0.05 mmol, is used even in a lower palladium/substrate ratio, e.g. 1 mol% concentration of the catalyst.