Transition-metal free synthesis of N-aryl carbazoles and their extended analogs

Herein, we describe a facile synthesis of N-arylated carbazoles via ladderization of fluorinated oligophenylenes. The reaction consists of two subsequent nucleophilic substitutions triggered by an electronic transfer from dimsyl anions. The reaction allows the effective one-pot formation of at least six C-N bonds with pronounced selectivity to the C-F bond placement.

Automated summary

A facile synthesis of N-arylated carbazoles via ladderization of fluorinated oligophenylenes is described, involving two subsequent nucleophilic substitutions triggered by an electronic transfer from dimsyl anions. The reaction allows effective one-pot formation of at least six C-N bonds with pronounced selectivity to the C-F bond placement.