Ruthenium-catalyzed C-H functionalization of indoles and indolines with 7-azabenzonorbornadienes: access to aminodihydronaphthyl indoles and indolines

Jia-Zhen Chen; Zhong-Xia Wang

doi:10.1039/d4ob00678j

Ruthenium-catalyzed C-H functionalization of indoles and indolines with 7-azabenzonorbornadienes: access to aminodihydronaphthyl indoles and indolines

Org Biomol Chem. 2024 Jun 26;22(25):5159-5169. doi: 10.1039/d4ob00678j.

Authors

Jia-Zhen Chen¹, Zhong-Xia Wang¹

Affiliation

¹ CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China. zxwang@ustc.edu.cn.

PMID: 38860854
DOI: 10.1039/d4ob00678j

Abstract

Indoles, indolines and hydronaphthylamines are ubiquitous structural motifs in natural products, pharmaceuticals, and biologically active molecules. In this paper, we report the synthesis of aminodihydronaphthyl-substituted indoles and indolines via a Ru-catalyzed carbamoyl-directed C-H functionalization of indoles and indolines with 7-azabenzonorbornadienes. In the presence of Cu(OAc)₂ and AgSbF₆, [Ru(p-cymene)Cl₂]₂ catalyzes the reaction of 1-carbamoylindoles with 7-azabenzonorbornadienes to produce 2-(1-amino-1,2-dihydronaphthalen-2-yl)indoles. Under the same conditions, the reaction of 1-carbamoylindolines with 7-azabenzonorbornadienes affords 7-(1-amino-1,2-dihydronaphthalen-2-yl)indolines. In both cases, the reactions yield cis-configured products.