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Iodine(III)-Enabled Distal C–H Functionalization of Biarylsulfonanilides

Author:
Bal, Ankita, Maiti, Saikat, Mal, Prasenjit
Source:
Journal of organic chemistry 2018 v.83 no.18 pp. 11278-11287
ISSN:
1520-6904
Subject:
carbazoles, carbon-hydrogen bond activation, chemical bonding, chemical structure, dehydrogenation, iodine, ions
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.
Agid:
6146230