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

The transient directing group promoted C­(sp2)–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-acyl acridines through direct C–H amination f...

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Bibliographic Details
Published in:Organic letters 2018-07, Vol.20 (13), p.4010-4014
Main Authors: Kim, Saegun, Han, Sang Hoon, Mishra, Neeraj Kumar, Chun, Rina, Jung, Young Hoon, Kim, Hyung Sik, Park, Jung Su, Kim, In Su
Format: Article
Language:English
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Summary:The transient directing group promoted C­(sp2)–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-acyl acridines through direct C–H amination followed by acid-mediated cyclization. A range of substrate scopes and functional group tolerance were observed.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01571