Dual Gold-Catalyzed Formal Tetradehydro-Diels-Alder Reactions for the Synthesis of Carbazoles and Indolines
Dual Gold-Catalyzed Formal Tetradehydro-Diels-Alder Reactions for the Synthesis of Carbazoles and Indolines
复制标题
双金催化甲醛四氢-狄尔斯-阿尔德反应合成咔唑和二氢吲哚
DOI：
10.1002/chem.201804529
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发表时间：
2018-12-05
影响因子：
4.3
通讯作者：
Zi, Weiwei
中科院分区：
文献类型：
--
作者：
Wang, Hong-Fa;Wang, Shi-Yue;Zi, Weiwei
这项工作报道了用于合成含氮芳香杂环的双金催化四氢-狄尔斯-阿尔德反应。在催化体系（IPrAuNTf2/DIPEA）下，二氢吲哚和咔唑以及其他含氮芳香杂环化合物的产率较高，且具有良好的官能团耐受性。与传统的热四氢-狄尔斯-阿尔德反应不同，该方案不需要稀释反应浓度和自由基抑制剂。实验数据支持涉及金亚乙烯基物种的机制，该机制经历 6 pi 电环化，然后进行 1,2-氢转移。
This work reports a dual gold-catalyzed tetradehydro-Diels-Alder reaction for the synthesis of nitrogen-containing aromatic heterocycles. Under the catalytic system (IPrAuNTf2/DIPEA), indolines and carbazoles as well as other N-containing aromatic heterocycles were prepared in high yields with good functional group tolerance. Unlike the traditional thermal tetradehydro-Diels-Alder reactions, diluted reaction concentration and radical prohibitors are not required for this protocol. Experimental data support a mechanism involving gold vinylidene species, which undergoes a 6 pi electrocyclization, followed with 1,2-hydrogen shift.