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A Visible Light and Iron‐mediated Carbocationic Route to Polysubstituted 1‐Halonaphthalenes by Benzannulation using Allylbenzenes and Polyhalomethanes
Author(s) -
Roslan Irwan Iskandar,
Zhang Hongwei,
Ng KianHong,
Jaenicke Stephan,
Chuah GaikKhuan
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001249
Subject(s) - chemistry , intramolecular force , photochemistry , substituent , friedel–crafts reaction , alkylation , visible spectrum , metal , combinatorial chemistry , catalysis , medicinal chemistry , stereochemistry , organic chemistry , physics , optoelectronics
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 Fe III mediated Friedel‐Crafts alkylation, with the formation of two C sp 2 −C sp 2 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.