An unusual decarboxylative benzannulation and biaryl formation during copper(I)-promoted halogen atom transfer radical cyclization of 2-allylaryl trichloroacetates |
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Authors: | Ram N Ram Ram K Tittal Shailesh Upreti |
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Institution: | Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi 110 016, India |
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Abstract: | CuCl/bpy-promoted halogen atom transfer radical cyclization of 2-allylaryl trichloroacetates in refluxing benzene gave benzannulated chloroarenes and benzannulated symmetrical biaryls along with reductive dehalogenation products. The unusual decarboxylative benzannulation and biaryl formation might be explained by a further intramolecular radical addition on the benzene ring of the eight-membered lactone intermediate, initially formed through 8-endo-trig halogen atom transfer radical cyclization, followed by decarboxylation, radical dimerization and dehydrochlorination reactions. |
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Keywords: | Benzannulation Biaryls Chloroarenes HATRC Decarboxylation CuCl/bpy |
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