PtIV-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation

PtIV-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation
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DOI:
10.1021/ol034177k
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发表时间:
2003-04-03
期刊:
影响因子:
5.2
通讯作者:
Sames, D
Sames, D
中科院分区:
化学1区
文献类型:
--
作者:
Pastine, SJ;Youn, SW;Sames, D

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我们在此报道,PtCl 4已被证明是具有上级先前已知方法的效率和底物范围的加氢芳基化催化剂。该催化剂表现出与具有不同结构特征的芳烃-炔底物(包括炔丙基醚、炔丙基胺和炔酸酯)一致的性能,提供良好至优异的6-内型产物(色烯、二氢喹啉和香豆素)产率。相比之下,Pt(II)、Pd(II)和Ga(III)盐显示出对炔部分上的取代敏感。
[GRAPHICS]We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.