Directed nucleophilic aromatic substitution reaction
Yasuyuki Nitta1, Yusei Nakashima1, Michinori Sumimoto1
1Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi, 755-8611, Japan. nisikata@yamaguchi-u.ac.jp.
Abstract:
In this study, we discovered a directed nucleophilic aromatic substitution reaction, "directed SNAr (dSNAr)," in the reaction of ortho-iodobezamides and amine in the presence of pyridine. The reaction proceeded ortho-specifically and did not require a strong electron-withdrawing group on the arene substrate. Most reactions proceeded at room temperature in the presence of Py, and a wide range of amine nucleophiles can be applied. Furthermore, the reactions with benzamide substituted with multiple halogens were found to be 100% ortho-selective.
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