Divergent Functionalization of Indoles with Acryloyl Silanes via Rhodium-Catalyzed C-H Activation
Ping Lu1, Chao Feng1,2, Teck-Peng Loh1,2
1†Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
Abstract:
A protocol enabled by rhodium-catalyzed C-H functionalization of indoles with acryloyl silanes was developed, providing a convenient and highly effective method for the synthesis of functionalized acylsilane derivatives. By tuning the reaction condition, this C-H-activation-initiated reaction proceeds divergently with acryloyl silianes to selectively afford alkylation or alkenylation products via hydroarylation or oxidative cross-coupling, respectively. The mild reaction conditions employed in both cases enable the tolerance of a wide scope of functionalities as well as high reaction efficiency. Furthermore, polycyclic indole derivatives were easily accessed from 2-alkenylation products through a visible-light-induced reaction cascade.
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