90-13-1Relevant articles and documents
Frater,Havinga
, p. 4603 (1969)
A Visible Light and Iron-mediated Carbocationic Route to Polysubstituted 1-Halonaphthalenes by Benzannulation using Allylbenzenes and Polyhalomethanes
Roslan, Irwan Iskandar,Zhang, Hongwei,Ng, Kian-Hong,Jaenicke, Stephan,Chuah, Gaik-Khuan
, p. 1007 - 1013 (2020/12/30)
A wide array of polysubstituted 1-bromo and chloronaphthalenes are obtained from coupling of allylbenzenes and polyhalomethanes. The reaction is mediated by iron metal under visible light irradiation and proceeds via a Kharasch addition intermediate followed by intramolecular FeIII mediated Friedel-Crafts alkylation, with the formation of two Csp2?Csp2 bonds in the process. This method gives easy access to 1-halonaphthalenes with substituent(s) at C-5 to C-8 that are otherwise hard to synthesize. (Figure presented.).
Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation
Rogers, David A.,Bensalah, Adam T.,Espinosa, Alvaro Tomas,Hoerr, John L.,Refai, Fares H.,Pitzel, Amy K.,Alvarado, Juan J.,Lamar, Angus A.
supporting information, p. 4229 - 4233 (2019/06/17)
Heteroarenes and arenes that contain electron-withdrawing groups are chlorinated in good to excellent yields (scalable to gram scale) using trichloroisocyanuric acid (TCCA) and catalytic Brilliant Green (BG). Visible-light activation of BG serves to amplify the electrophilic nature of TCCA, providing a mild alternative approach to acid-promoted chlorination of deactivated (hetero)aromatic substrates. The utility of the TCCA/BG system is demonstrated through comparison to other chlorinating reagents and by the chlorination of pharmaceuticals including caffeine, lidocaine, and phenazone.