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金(I)催化的2-(1-炔基)-2-烯-1-酮与乙烯基重氮酮之间的反应用于非对称杂芳基取代三芳基甲烷的发散合成:进攻路径的比较。

Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: versus -Attack Paths.

作者信息

Kardile Rahul Dadabhau, Liu Rai-Shung

机构信息

Frontier Research Center of Matter Science and Technology, Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan, ROC.

出版信息

Org Lett. 2020 Nov 6;22(21):8229-8233. doi: 10.1021/acs.orglett.0c02765. Epub 2020 Oct 12.

DOI:10.1021/acs.orglett.0c02765
PMID:33043671
Abstract

Gold-catalyzed synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes using 2-(1-alkynyl)-2-alken-1-ones and vinyldiazo ketones is described. In this catalytic sequence, vinyldiazo ketones attack gold-containing 3-furylbenzyl cations to form the observed C(1)-addition products. We also note that vinyldiazo ketones can be thermally cyclized to yield pyrazole derivatives, which can react with 3-furylbenzyl cations to afford pyrazole-containing triarylmethanes, corresponding to a N(5)-addition path.

摘要

描述了使用2-(1-炔基)-2-烯-1-酮和乙烯基重氮酮通过金催化合成非对称杂芳基取代的三芳基甲烷。在这个催化过程中,乙烯基重氮酮进攻含金的3-呋喃基苄基阳离子以形成观察到的C(1)-加成产物。我们还注意到乙烯基重氮酮可以热环化生成吡唑衍生物,其可与3-呋喃基苄基阳离子反应得到含吡唑的三芳基甲烷,这对应于N(5)-加成路径。

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