Hg(OAc)(2).0.1Sc(OTf)(3)-catalyzed cycloisomerization of 2-(4-pentynyl)furan.

Hg(OAc)(2).0.1Sc(OTf)(3)-catalyzed cycloisomerization of 2-(4-pentynyl)furan.
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DOI:
10.1021/ol070335m
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发表时间:
2007-02
期刊:
影响因子:
5.2
通讯作者:
Hirofumi Yamamoto;Ikuo Sasaki;H. Imagawa;M. Nishizawa*
Hirofumi Yamamoto;Ikuo Sasaki;H. Imagawa;M. Nishizawa*
中科院分区:
化学1区
文献类型:
--
作者:
Hirofumi Yamamoto;Ikuo Sasaki;H. Imagawa;M. Nishizawa*

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[结构:见正文]。在Hg(OTf)2.3TMU催化下的3-(4-戊炔基)呋喃的Friedel-Crafts型反应生成了外环产物,而2-(4-戊炔基)呋喃的反应产率很低。发现10:1的HgOAc(OAc)2和Sc(OTf)3混合试剂对后一种转化具有显著的催化活性。实际的反应物种被推测为Hg(OAc)(OTf),它是通过将两种试剂混合在一起在原位有效地生成的。
[structure: see text]. Although the Hg(OTf)2.3TMU-catalyzed Friedel-Crafts-type reaction of 3-(4-pentynyl)furan afforded the exo cyclization product, the reaction of 2-(4-pentynyl)furan furnished a very low yield. We found a 10:1 mixed reagent of Hg(OAc)2 and Sc(OTf)3 showed remarkable catalytic activity for the latter transformation. The actual reacting species is presumed to be Hg(OAc)(OTf), which is efficiently generated in situ by mixing the two reagents.