Ligand-Dependant Selective Synthesis of Mono- and Dialkenylcarbazoles through Rhodium(III)-Catalyzed C-H Alkenylation

Rikuto Tanaka; Shiho Ochiai; Asumi Sakai; Yoshinosuke Usuki; Bubwoong Kang; Tetsuro Shinada; Tetsuya Satoh

doi:10.1002/asia.202201210

Ligand-Dependant Selective Synthesis of Mono- and Dialkenylcarbazoles through Rhodium(III)-Catalyzed C-H Alkenylation

Chem Asian J. 2023 Feb 14;18(4):e202201210. doi: 10.1002/asia.202201210. Epub 2023 Jan 13.

Authors

Rikuto Tanaka¹, Shiho Ochiai¹, Asumi Sakai¹, Yoshinosuke Usuki¹, Bubwoong Kang², Tetsuro Shinada¹, Tetsuya Satoh¹

Affiliations

¹ Department of Chemistry, Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka, 558-8585, Japan.
² Graduate School of Agricultural Science, Kobe University, 1-1 Rokkodai, Nada-ku, Kobe, Hyogo, 657-8501, Japan.

PMID: 36600559
DOI: 10.1002/asia.202201210

Abstract

The C-H alkenylation of N-acetylcarbazoles proceeds smoothly at the C1-position in the presence of a cationic Cp*Rh(III) catalyst to produce 1-alkenylcarbazoles. The use of a cationic Cp^E Rh(III) catalyst enables further alkenylation to give 1,8-dialkenylcarbazoles. The direct alkenylation procedure in combination with the ready removal of the acetyl directing group provides a straightforward synthetic pathway to 1- and/or 8-alkenyl-N-H-carbazole derivatives. One of 1-alkenyl-N-H-carbazoles obtained by the present C-H alkenylation/deacetylation exhibits solvatochromism.

Keywords: Alkenylation; Carbazole; C−C coupling; C−H activation; Rhodium.

Abstract

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