Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp 3 )−H and C(sp 2 )−H under Rhodium(III) Catalysis

Songjie Yu, Guodong Tang, Yingzi Li, Xukai Zhou, Yu Lan*, Xingwei Li

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

193 Citations (Scopus)

Abstract

Previous direct C−H nitrogenation suffered from simple amidation/amination with limited atom-economy and is mostly limited to C(sp 2 )−H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp 2 )−H and C(sp 3 )−H bonds under rhodium(III) catalysis, thus affording a nucleophilic aniline tethered to an electrophilic carbonyl. A tridendate rhodium(III) complex has been isolated as the resting state of the catalyst, and DFT studies established the intermediacy of a nitrene species.

Original languageEnglish
Pages (from-to)8696-8700
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number30
Early online date28 Apr 2016
DOIs
Publication statusPublished - 18 Jul 2016

Keywords

  • amination
  • arenes
  • C−H activation
  • reaction mechanisms
  • rhodium

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