Department of Chemistry, University of Delhi, Delhi-110007, India.
Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau cedex, France.
Org Lett. 2022 Jul 22;24(28):5018-5022. doi: 10.1021/acs.orglett.2c01665. Epub 2022 Jul 7.
An unconventional approach for the regioselective synthesis of polyaromatic biaryls via site-selective Ag-catalyzed twofold electrophilic cycloisomerization followed by Au-catalyzed double C-H activation is described. The developed process allows the synthesis of highly decorated biaryls with excellent regioselectivity. As revealed by DFT computations, the reaction represents a rare example of C1-C5 - and C1-C6 - cycloaromatization. The formation of the 6-membered ring is predicted to be the fruit of an uncommon SEAr on a vinyl carbocation.
本文描述了一种通过 Ag 催化的双亲电环化反应实现区域选择性合成多芳基联芳烃的非常规方法，随后通过 Au 催化的双 C-H 活化反应进一步进行。该方法可实现高度装饰的联芳烃的合成，具有优异的区域选择性。通过 DFT 计算表明，该反应代表了 C1-C5 和 C1-C6 环芳构化的罕见实例。预测六元环的形成是乙烯基碳正离子上不常见的 SEAr 的结果。
