Synthesis 2021; 53(17): 2984-2994
DOI: 10.1055/s-0040-1706025
special topic
Bond Activation – in Honor of Prof. Shinji Murai

Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes

Hikaru Watanabe
a   Department of Applied Chemistry and Biotechnology, Okayama University of Science, 1-1, Ridai-cho, Kita-ku,Okayama 700-0005, Japan
,
Kazuki Nakajima
a   Department of Applied Chemistry and Biotechnology, Okayama University of Science, 1-1, Ridai-cho, Kita-ku,Okayama 700-0005, Japan
,
Kento Ekuni
a   Department of Applied Chemistry and Biotechnology, Okayama University of Science, 1-1, Ridai-cho, Kita-ku,Okayama 700-0005, Japan
,
Ryota Edagawa
a   Department of Applied Chemistry and Biotechnology, Okayama University of Science, 1-1, Ridai-cho, Kita-ku,Okayama 700-0005, Japan
,
Yuta Akagi
a   Department of Applied Chemistry and Biotechnology, Okayama University of Science, 1-1, Ridai-cho, Kita-ku,Okayama 700-0005, Japan
,
a   Department of Applied Chemistry and Biotechnology, Okayama University of Science, 1-1, Ridai-cho, Kita-ku,Okayama 700-0005, Japan
,
b   Department of Chemistry, Okayama University of Science, 1-1, Ridai-cho, Kita-ku, Okayama 700-0005, Japan
,
Akihiro Orita
a   Department of Applied Chemistry and Biotechnology, Okayama University of Science, 1-1, Ridai-cho, Kita-ku,Okayama 700-0005, Japan
› Institutsangaben
A. Orita thanks JSPS (JP18K05134), JSPS Innovative Areas (JP18H04430), Okayama Prefecture Industrial Promotion Foundation, and OUS Research Project (OUS-RP-29-1 and OUS-RP-19-4). Y. Okuda thanks to JSPS (JP19K15574), Wesco Scientific Promotion Foundation, and OUS Research Project (OUS-RP-29-1 and OUS-RP-20-6) for financial support.


Abstract

The Sonogashira coupling of 1,3,6,8-tetrabromopyrene with 4-[(–)-β-citronellyloxy]phenylethyne was employed to synthesize 1,3,6,8-tetra[4-(citronellyloxy)phenylethynyl]pyrene. The pyrene derivative catalyzed the reductive desulfonylation of ethenyl sulfones via visible-light irradiation (514 nm green light-emitting diodes) in the presence of i-Pr2NEt. The β-citronellyloxy groups provided the sufficient solubility to the highly π-expanded pyrene catalyst, and their polar oxygen functionalities enabled the easy separation of the catalyst from the products via column chromatography.

Supporting Information



Publikationsverlauf

Eingereicht: 06. Januar 2021

Angenommen nach Revision: 25. Januar 2021

Artikel online veröffentlicht:
22. Februar 2021

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