Carbocation versus carbene controlled chemoselectivity: Dft study on gold- And silver-catalyzed alkylation/cyclopropanation of indoles with vinyl diazoesters

Density functional theory calculations were performed to investigate the catalyst-controlled selective functionalization of indoles with vinyl diazoacetates. The detailed reaction mechanism was established, and different roles of carboncation or carbene intermediates in defining an experimentally observed chemo- and regioselectivity were fully rationalized. © 2020 American Chemical Society.

Authors
Fang R. 1, 2 , Yang L. 1, 2 , Zhou L. 2 , Kirillov A.M. 3, 4 , Yang L. 1, 2
Journal
Organic Letters
Issue number
10
Language
English
Pages
4043-4048
State
Published
Link
External link
DOI
10.1021/ACS.ORGLETT.0C01476
Volume
22
Year
2020
Organizations
  • 1 College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an, 710021, China
  • 2 State Key Laboratory of Applied Organic Chemistry and Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China
  • 3 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001, Lisbon, Portugal
  • 4 Research Institute of Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya st, Moscow, 117198, Russian Federation
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