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Iodine(III)-Enabled Distal C-H Functionalization of Biarylsulfonanilides
Ankita Bal1, Saikat Maiti1, Prasenjit Mal1
1School of Chemical Sciences , National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar , PO Bhimpur-Padanpur, Via Jatni, District Khurda , Odisha 752050 , India.
Abstract:
Here we report a metal-free C-N coupling reaction for carbazole synthesis by distal (- meta) C-H bond functionalization. Nitrenium ion, a potential synthetic intermediate, was generated in situ from reactions of iodine(III) reagents and biarylsulfonanilides. Following, nitrenium ions were used for intramolecular dehydrogenative C-N coupling reactions via 1,2-alkyl (methyl or ethyl) migration by the expense of C-H bond functionalization at the distal position toward synthesis of 1,2,4-trialkyl-substituted carbazoles. The iodine(III) condition was either maintained by using a stoichiometric amount of phenyliodine diacetate (PIDA) or in-situ generated from iodobenzene (PhI)- meta-chloroperbenzoic acid ( mCPBA) combination.
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