Boron-mediated sequential alkyne insertion and C–C coupling reactions affording extended π-conjugated molecules

Yoshiaki Shoji, Naoki Tanaka, Sho Muranaka, Naoki Shigeno, Haruka Sugiyama, Kumiko Takenouchi, Fatin Hajjaj and Takanori Fukushima ()
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Yoshiaki Shoji: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Naoki Tanaka: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Sho Muranaka: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Naoki Shigeno: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Haruka Sugiyama: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Kumiko Takenouchi: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Fatin Hajjaj: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology
Takanori Fukushima: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology

Nature Communications, 2016, vol. 7, issue 1, 1-7

Abstract: Abstract C–C bond coupling reactions illustrate the wealth of organic transformations, which are usually mediated by organotransition metal complexes. Here, we show that a borafluorene with a B–Cl moiety can mediate sequential alkyne insertion (1,2-carboboration) and deborylation/Csp2–Csp2 coupling reactions, leading to aromatic molecules. The first step, which affords a borepin derivative, proceeds very efficiently between the borafluorene and various alkynes by simply mixing these two components. The second step is triggered by a one-electron oxidation of the borepin derivative, which results in the formation of a phenanthrene framework. When an excess amount of oxidant is used in the second step, the phenanthrene derivatives can be further transformed in situ to afford dibenzo[g,p]chrysene derivatives. The results presented herein will substantially expand the understanding of main group chemistry and provide a powerful synthetic tool for the construction of a wide variety of extended π-conjugated systems.

Date: 2016
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DOI: 10.1038/ncomms12704

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