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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Published on: June 20, 2014

Nickel-Catalyzed C-H Chalcogenation of Anilines

Thomas Müller¹, Lutz Ackermann²

¹Institut für Organische und Biomolekulare Chemie, Georg-August-Universität, Tammannstraße 2, 37077, Göttingen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|August 9, 2016

Abstract:

The C-H thiolation of aniline derivatives was accomplished with a versatile nickel(II) catalyst under ligand-free conditions. The robust nature of the nickel catalysis system was reflected by the C-H thiolation with a good functional group tolerance and an ample scope, employing anilines possessing removable directing groups. The widely applicable nickel catalyst also allowed for aniline C-H selenylations, while mechanistic studies provided strong support that the rate-determining step is the C-H activation.

Keywords:

C−H activation nickel reaction mechanisms selenylation sulfenylation

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