Highly selective gold-catalyzed arene synthesis
Highly selective gold-catalyzed arene synthesis
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DOI：
10.1021/ja005570d
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发表时间：
2000-11-22
影响因子：
15
通讯作者：
Bats, JW
中科院分区：
文献类型：
--
作者：
Hashmi, ASK;Frost, TM;Bats, JW
The classic route to aromatic compounds with specific substitution patterns is the aromatic substitution which introduces or exchanges substituents at an already existing arene. 1 A different mechanism but the same synthetic principle is applied in the different transition-metal-catalyzed (cross-) coupling reactions2 or ortho-metalation and subsequent functionalization reactions. 3 Other approaches assemble the arene, eg use cycloaddition reactions such as the Diels-Alder reaction followed by a subsequent oxidation of the unsaturated six-membered ring to an arene. 4 Some major achievements in this field of cycloadditions or cycloisomerizations of the past years stem from transition metal catalysis. 5 For arene synthesis Vollhardt’s [2+ 2+ 2] cycloaddition6 and variations thereof7 as well as the Dötz reaction8 are among the most prominent.We now want to report our results concerning the synthesis of highly substituted arenes, more specifical phenols, by gold catalysis. Gold-catalyzed homogeneous organic reactions are quite rare: the only examples that reached some importance are the Ito-Hayashi aldol reaction9 and the addition of O-or N-nucleophiles to unsaturated compounds first described by Utimoto10 and later improved by Teles. 11 Recently we reported new CO-and CC-bond formations catalyzed by gold; further investigation of these reactions led to the completely new results described here. 12
