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Updated: Jun 3, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Atom-efficient chlorinative dearomatization of naphthol, quinolinol, and isoquinolinol derivatives using
Jenna D Caudle1, Marlow K Ennis1, Dillon C Dodge1
1Department of Chemistry and Biochemistry, The University of Tulsa 800 South Tucker Drive, Tulsa, OK 74104, USA. angus-lamar@utulsa.edu.
Abstract:
A variety of dearomatized compounds have been prepared in moderate to excellent yields from planar scaffolds using trichloroisocyanuric acid (TCCA) as an atom-economical chlorinating agent. The method tolerates a broad range of functionalities and can take place in several green and/or sustainable solvents. Twenty-one examples of 1,1-dichlorinated products of dearomatized 2-naphthols and analogous heteroarenes (quinolinols, isoquinolinols, and quinazolinol) are reported along with five examples of monochlorinated dearomatized products. The utility of the 1,1-dichloronaphthalenone product as a reactive intermediate species is demonstrated in a two-step, one-pot reaction carried out in a green solvent. In a mechanistic investigation, the coordination of the chlorinating agent to the hydroxy substituent of the planar scaffold prior to chlorine transfer is implicated.
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