4.8 Article

Dual Role of Anthranils as Amination and Transient Directing Group Sources: Synthesis of 2-Acyl Acridines

Journal

ORGANIC LETTERS
Volume 20, Issue 13, Pages 4010-4014

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01571

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Funding

  1. National Research Foundation of Korea (NRF) grant - Korean government (MSIP) [2016R1A4A1011189, 2016R1C1B2014895, 2017R1A2B2004786]
  2. NRF [2017H1A2A1044843]

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The transient directing group promoted C-(sp(2))-H functionalization of benzaldehydes with anthranils by a cationic rhodium(III) catalyst is described. Notably, anthranils have been used as both transient directing groups and amination sources to afford 2-aryl acridines through direct C-H amination followed by acid-mediated cyclization. A range of substrate scopes and functional group tolerance were observed.

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