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Issue 1, 2017
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Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a rhodium-catalysed stitching reaction

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Abstract

A rhodium-catalysed stitching reaction between 2-(silylethynyl)arylboronates and 2-(silylethynyl)aryl bromides has been developed for the synthesis of unsymmetric dibenzo[a,e]pentalenes. The introduction of appropriately sized silyl groups on the starting substrates led to a high crossover selectivity without using an excess amount of either substrate. The present stitching reaction could produce a variety of unsymmetric dibenzo[a,e]pentalene derivatives, including those with electronically different substituents on the fused benzene rings as well as heteroarene fused compounds. Desilylative halogenation was also demonstrated to synthesise the corresponding halogenated dibenzo[a,e]pentalenes, which can be used as building blocks for further chemical transformations.

Graphical abstract: Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a rhodium-catalysed stitching reaction

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Publication details

The article was received on 12 Oct 2016, accepted on 02 Nov 2016 and first published on 14 Nov 2016


Article type: Edge Article
DOI: 10.1039/C6SC04560J
Citation: Chem. Sci., 2017,8, 101-107
  • Open access: Creative Commons BY-NC license
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    Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a rhodium-catalysed stitching reaction

    K. Takahashi, S. Ito, R. Shintani and K. Nozaki, Chem. Sci., 2017, 8, 101
    DOI: 10.1039/C6SC04560J

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