Synlett
DOI: 10.1055/s-0036-1588417
cluster
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed N-Arylation Using N-Trimethylsilyl-carbazole

Yasunori Minami*a, Takeshi Komiyamab, Kenta Shimizub, Shu-ichi Unob, Tamejiro Hiyama*a, Osamu Gotoc, Hideyuki Ikehirad
  • aResearch and Development Initiative, Chuo University, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yminami@kc.chuo-u.ac.jp   Email: thiyama@kc.chuo-u.ac.jp
  • bFaculty of Science and Engineering, Chuo University, Kasuga, Bunkyo-ku, Tokyo 112-8551 Japan
  • cSumitomo Chemical, 3-1-98 Kasugadenaka, Konohana-ku, Osaka, 554-8558, Japan
  • dSumika Technical Information Service, 4-6-17 Koraibashi,Chuo-ku, Osaka, 541-0043, Japan
Supported by: Grants-in-Aid for Young Scientists (B) 25870747
Supported by: Japan Science and Technology Agency ACT-C
Further Information

Publication History

Received: 06 March 2017

Accepted after revision: 11 April 2017

Publication Date:
08 May 2017 (eFirst)

Published as part of the Cluster Silicon in Synthesis and Catalysis

Abstract

Nickel-catalyzed N-arylation reaction of N-trimethylsilyl-carbazole using aryl bromides is found to proceed in the presence of sodium acetate, giving N-aryl-carbazoles in high yields. Under these conditions, N-trimethylsilyl-carbazole could react with aryl bromides selectively even in the presence of other N-trimethylsilyl-amines or N-H-amines. This arylation reaction was applied to the polymerization to provide a polycarbazole.

Supporting Information