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Synfacts 2014; 10(5): 0473
DOI: 10.1055/s-0033-1341163
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Extending Arenes via C–H Activation with Rhodium

Contributor(s):
Timothy M. Swager
,
John B. Goods
Pham MV, Cramer N * École Polytechnique Fédérale de Lausanne, Switzerland
Aromatic Homologation by Non-Chelate-Assisted RhIII-Catalyzed C–H Functionalization of Arenes with Alkynes.

Angew. Chem. Int. Ed. 2014;
53: 3484-3487
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Publication History

Publication Date:
17 April 2014 (online)

 
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Key words

polyaromatic hydrocarbons - rhodium - C–H functionalization

Significance

Extending the conjugation length of arenes is of great interest to the materials chemistry community due to the impartation of new electrical and photophysical properties. The previously reported method for rhodium-catalyzed arene ­homologation was achieved with a boronic acid functionalized substrates (J. Org. Chem. 2011, 76, 2867); in contrast, Pham and Cramer report a C–H functionalization to achieve the same transformation.


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Comment

While dibutyl alkynes were used most prominently in this paper, the authors were also able to demonstrate that other alkynes, including those bearing aryl groups, could be incorporated. A proposed mechanism for the transformation is included in the paper.


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