Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation.
J Org Chem. 2021 Dec 17;86(24):17804-17815. doi: 10.1021/acs.joc.1c02119. Epub 2021 Nov 23.
Gold(I)-catalyzed [4 + 2] cycloaddition of indolylynamides and cyanamides (aminonitriles) is an efficient redox-neutral and atom-economic route to diversely substituted 1,3-diamino-β-carbolines. The protocol operates under mild conditions (PhPAuNTf 5 mol %, DCE, 60 °C) with a good tolerance to functional groups (23 examples and yields up to 98%). The obtained β-carboline systems represent a versatile synthetic platform with modifiable substituents for successive functionalizations. Control experiments indicate the crucial role of both the nature of reactants and the identity of employed catalysts in the developed cycloaddition.
金（I）催化吲哚亚胺酰胺和氰酰胺（氨基腈）的[4+2]环加成反应是一种高效的氧化还原中性和原子经济性方法，可用于合成各种取代的1,3-二氨基-β-咔啉。该反应在温和条件下（PhPAuNTf2 摩尔%，DCE，60°C）进行，对官能团具有良好的耐受性（23 个实例，产率高达 98%）。所得的β-咔啉体系代表了一种具有可修饰取代基的多功能合成平台，可用于后续的功能化。对照实验表明反应物的性质和所使用的催化剂的种类在开发的环加成反应中起着至关重要的作用。
